Ethyl 1-(2-hy-droxy-eth-yl)-2-(4-meth-oxy-phen-yl)-1H-benzimidazole-5-carboxyl-ate monohydrate.

In the title mol-ecule, C(19)H(20)N(2)O(4)·H(2)O, the benzimidazole ring system is essentially planar [maximum deviation = 0.013 (11) Å] and is inclined to the 4-meth-oxy-phenyl ring by 30.98 (5)°. In the crystal, O-H⋯O and O-H⋯N hydrogen bonds involving the water mol-ecule link neighbouring mol-ecules, forming a two-dimensional network lying parallel to the bc plane. There are also C-H⋯π and π-π inter-actions present. The latter involve inversion-related benzimidazole rings with centroid-centroid distances of 3.5552 (8) and 3.7466 (8) Å.

Related literature

For the synthesis of the title compound, see: Arumugam et al. (2010 ▶). For the biological activity of benzimidazole derivatives, see: Cosar & Julou (1959 ▶); Gudmundsson et al. (1999 ▶); De Clercq et al. (1993 ▶); Spasov et al. (1999 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H20N2O4·H2O

M = 358.39

Monoclinic,

a = 10.6364 (11) Å

b = 9.5089 (10) Å

c = 19.3765 (17) Å

β = 112.899 (5)°

V = 1805.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.35 × 0.25 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.967, T max = 0.983

13982 measured reflections

3140 independent reflections

2856 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 1.02

3140 reflections

249 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812001262/su2368sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001262/su2368Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001262/su2368Isup3.cml

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

C19H20N2O4·H2O	F(000) = 760
Mr = 358.39	Dx = 1.319 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9429 reflections
a = 10.6364 (11) Å	θ = 2.9–25.0°
b = 9.5089 (10) Å	µ = 0.10 mm−1
c = 19.3765 (17) Å	T = 293 K
β = 112.899 (5)°	Block, colourless
V = 1805.3 (3) Å3	0.35 × 0.25 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3140 independent reflections
Radiation source: fine-focus sealed tube	2856 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 83.66 pixels mm-1	θmax = 25.0°, θmin = 2.9°
φ and ω scan	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.967, Tmax = 0.983	l = −23→21
13982 measured reflections

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) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0382P)2 + 0.7017P] where P = (Fo2 + 2Fc2)/3
3140 reflections	(Δ/σ)max < 0.001
249 parameters	Δρmax = 0.19 e Å−3
3 restraints	Δρmin = −0.20 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
O1	0.03607 (9)	0.11092 (10)	−0.10495 (5)	0.0273 (2)
O2	0.13828 (10)	0.11955 (10)	0.02067 (5)	0.0318 (2)
O3	1.05219 (9)	−0.64334 (10)	0.19548 (5)	0.0299 (2)
O4	0.56061 (11)	−0.49083 (10)	−0.20486 (5)	0.0308 (2)
H4B	0.5547 (19)	−0.4247 (16)	−0.2358 (9)	0.055 (6)*
N1	0.54707 (10)	−0.27695 (10)	−0.04766 (5)	0.0195 (2)
N2	0.53184 (10)	−0.24427 (10)	0.06353 (6)	0.0207 (2)
C1	0.79606 (13)	−0.37042 (14)	0.14242 (7)	0.0246 (3)
H1A	0.7743	−0.2930	0.1650	0.029*
C2	0.90530 (13)	−0.45375 (15)	0.18365 (7)	0.0277 (3)
H2A	0.9560	−0.4328	0.2337	0.033*
C3	0.94031 (12)	−0.56962 (14)	0.15058 (7)	0.0235 (3)
C4	0.86192 (13)	−0.60221 (13)	0.07631 (7)	0.0243 (3)
H4A	0.8838	−0.6799	0.0540	0.029*
C5	0.75072 (13)	−0.51868 (13)	0.03529 (7)	0.0231 (3)
H5A	0.6979	−0.5421	−0.0142	0.028*
C6	0.71694 (12)	−0.40026 (13)	0.06695 (7)	0.0206 (3)
C7	0.59923 (12)	−0.30890 (12)	0.02771 (7)	0.0194 (3)
C8	0.43855 (12)	−0.18642 (12)	−0.06055 (7)	0.0197 (3)
C9	0.34925 (13)	−0.12055 (13)	−0.12536 (7)	0.0219 (3)
H9A	0.3561	−0.1332	−0.1714	0.026*
C10	0.24989 (12)	−0.03538 (13)	−0.11789 (7)	0.0224 (3)
H10A	0.1875	0.0093	−0.1600	0.027*
C11	0.24092 (12)	−0.01465 (12)	−0.04771 (7)	0.0217 (3)
C12	0.33239 (12)	−0.07870 (12)	0.01676 (7)	0.0212 (3)
H12A	0.3277	−0.0634	0.0631	0.025*
C13	0.43118 (12)	−0.16652 (12)	0.00957 (7)	0.0196 (3)
C14	0.13541 (13)	0.07845 (13)	−0.03903 (7)	0.0234 (3)
C15	−0.06792 (14)	0.20632 (16)	−0.10130 (8)	0.0328 (3)
H15A	−0.0296	0.2992	−0.0858	0.039*
H15B	−0.1042	0.1723	−0.0656	0.039*
C16	−0.17773 (17)	0.2119 (2)	−0.17790 (10)	0.0550 (5)
H16A	−0.2463	0.2782	−0.1785	0.082*
H16B	−0.2182	0.1205	−0.1914	0.082*
H16C	−0.1395	0.2407	−0.2131	0.082*
C17	1.10325 (14)	−0.74776 (15)	0.15978 (7)	0.0292 (3)
H17A	1.1895	−0.7819	0.1946	0.044*
H17B	1.1148	−0.7070	0.1173	0.044*
H17C	1.0396	−0.8243	0.1435	0.044*
C18	0.59596 (12)	−0.31970 (13)	−0.10568 (7)	0.0213 (3)
H18A	0.6892	−0.3533	−0.0822	0.026*
H18B	0.5952	−0.2393	−0.1366	0.026*
C19	0.50589 (13)	−0.43538 (13)	−0.15438 (7)	0.0235 (3)
H19A	0.4971	−0.5104	−0.1226	0.028*
H19B	0.4155	−0.3979	−0.1826	0.028*
O5	0.54527 (11)	−0.26408 (11)	−0.28926 (5)	0.0342 (2)
H5B	0.510 (2)	−0.1856 (14)	−0.2842 (12)	0.062 (6)*
H5C	0.542 (2)	−0.267 (2)	−0.3338 (7)	0.061 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0236 (5)	0.0305 (5)	0.0275 (5)	0.0048 (4)	0.0096 (4)	0.0009 (4)
O2	0.0326 (5)	0.0363 (5)	0.0274 (5)	0.0044 (4)	0.0126 (4)	−0.0064 (4)
O3	0.0288 (5)	0.0376 (5)	0.0214 (5)	0.0106 (4)	0.0077 (4)	−0.0008 (4)
O4	0.0533 (6)	0.0220 (5)	0.0257 (5)	0.0010 (4)	0.0248 (5)	−0.0003 (4)
N1	0.0216 (5)	0.0199 (5)	0.0179 (5)	−0.0012 (4)	0.0086 (4)	−0.0012 (4)
N2	0.0217 (5)	0.0214 (5)	0.0193 (5)	−0.0026 (4)	0.0085 (4)	−0.0012 (4)
C1	0.0262 (6)	0.0284 (7)	0.0211 (6)	0.0019 (5)	0.0113 (5)	−0.0031 (5)
C2	0.0274 (7)	0.0361 (7)	0.0182 (6)	0.0024 (6)	0.0074 (5)	−0.0032 (5)
C3	0.0216 (6)	0.0276 (6)	0.0220 (6)	0.0015 (5)	0.0092 (5)	0.0030 (5)
C4	0.0282 (7)	0.0207 (6)	0.0246 (6)	−0.0003 (5)	0.0111 (5)	−0.0021 (5)
C5	0.0255 (6)	0.0226 (6)	0.0191 (6)	−0.0044 (5)	0.0065 (5)	−0.0017 (5)
C6	0.0212 (6)	0.0215 (6)	0.0207 (6)	−0.0039 (5)	0.0099 (5)	0.0011 (5)
C7	0.0213 (6)	0.0186 (6)	0.0187 (6)	−0.0057 (5)	0.0083 (5)	−0.0018 (5)
C8	0.0210 (6)	0.0175 (6)	0.0212 (6)	−0.0044 (5)	0.0089 (5)	−0.0026 (5)
C9	0.0262 (6)	0.0221 (6)	0.0182 (6)	−0.0035 (5)	0.0095 (5)	−0.0023 (5)
C10	0.0229 (6)	0.0211 (6)	0.0205 (6)	−0.0024 (5)	0.0055 (5)	0.0001 (5)
C11	0.0211 (6)	0.0188 (6)	0.0246 (6)	−0.0041 (5)	0.0084 (5)	−0.0030 (5)
C12	0.0236 (6)	0.0213 (6)	0.0207 (6)	−0.0062 (5)	0.0109 (5)	−0.0043 (5)
C13	0.0203 (6)	0.0187 (6)	0.0194 (6)	−0.0050 (5)	0.0071 (5)	−0.0015 (5)
C14	0.0232 (6)	0.0214 (6)	0.0252 (7)	−0.0043 (5)	0.0091 (5)	−0.0016 (5)
C15	0.0277 (7)	0.0369 (8)	0.0368 (8)	0.0092 (6)	0.0159 (6)	0.0039 (6)
C16	0.0359 (9)	0.0788 (13)	0.0442 (10)	0.0216 (9)	0.0090 (8)	0.0018 (9)
C17	0.0282 (7)	0.0342 (7)	0.0264 (7)	0.0070 (6)	0.0120 (6)	−0.0001 (6)
C18	0.0252 (6)	0.0225 (6)	0.0195 (6)	0.0001 (5)	0.0123 (5)	0.0004 (5)
C19	0.0302 (7)	0.0231 (6)	0.0189 (6)	−0.0008 (5)	0.0115 (5)	−0.0008 (5)
O5	0.0533 (6)	0.0309 (5)	0.0247 (5)	0.0084 (5)	0.0219 (5)	0.0080 (4)

O1—C14	1.3391 (16)	C9—C10	1.3831 (18)
O1—C15	1.4533 (15)	C9—H9A	0.9300
O2—C14	1.2100 (16)	C10—C11	1.4135 (18)
O3—C3	1.3633 (15)	C10—H10A	0.9300
O3—C17	1.4324 (16)	C11—C12	1.3900 (18)
O4—C19	1.4200 (15)	C11—C14	1.4895 (17)
O4—H4B	0.854 (9)	C12—C13	1.3909 (17)
N1—C7	1.3794 (15)	C12—H12A	0.9300
N1—C8	1.3825 (16)	C15—C16	1.490 (2)
N1—C18	1.4677 (15)	C15—H15A	0.9700
N2—C7	1.3268 (16)	C15—H15B	0.9700
N2—C13	1.3838 (16)	C16—H16A	0.9600
C1—C2	1.3761 (19)	C16—H16B	0.9600
C1—C6	1.4033 (18)	C16—H16C	0.9600
C1—H1A	0.9300	C17—H17A	0.9600
C2—C3	1.3961 (18)	C17—H17B	0.9600
C2—H2A	0.9300	C17—H17C	0.9600
C3—C4	1.3887 (18)	C18—C19	1.5215 (17)
C4—C5	1.3893 (18)	C18—H18A	0.9700
C4—H4A	0.9300	C18—H18B	0.9700
C5—C6	1.3946 (17)	C19—H19A	0.9700
C5—H5A	0.9300	C19—H19B	0.9700
C6—C7	1.4695 (17)	O5—H5B	0.855 (9)
C8—C9	1.3940 (17)	O5—H5C	0.852 (9)
C8—C13	1.4040 (17)
C14—O1—C15	115.49 (10)	C11—C12—C13	117.71 (11)
C3—O3—C17	116.68 (10)	C11—C12—H12A	121.1
C19—O4—H4B	105.8 (13)	C13—C12—H12A	121.1
C7—N1—C8	106.98 (10)	N2—C13—C12	129.62 (11)
C7—N1—C18	129.31 (10)	N2—C13—C8	109.94 (10)
C8—N1—C18	123.63 (10)	C12—C13—C8	120.44 (11)
C7—N2—C13	105.60 (10)	O2—C14—O1	123.68 (12)
C2—C1—C6	121.14 (12)	O2—C14—C11	124.06 (12)
C2—C1—H1A	119.4	O1—C14—C11	112.26 (10)
C6—C1—H1A	119.4	O1—C15—C16	106.87 (12)
C1—C2—C3	120.24 (12)	O1—C15—H15A	110.3
C1—C2—H2A	119.9	C16—C15—H15A	110.3
C3—C2—H2A	119.9	O1—C15—H15B	110.3
O3—C3—C4	124.72 (11)	C16—C15—H15B	110.3
O3—C3—C2	115.81 (11)	H15A—C15—H15B	108.6
C4—C3—C2	119.47 (11)	C15—C16—H16A	109.5
C3—C4—C5	119.97 (12)	C15—C16—H16B	109.5
C3—C4—H4A	120.0	H16A—C16—H16B	109.5
C5—C4—H4A	120.0	C15—C16—H16C	109.5
C4—C5—C6	121.18 (11)	H16A—C16—H16C	109.5
C4—C5—H5A	119.4	H16B—C16—H16C	109.5
C6—C5—H5A	119.4	O3—C17—H17A	109.5
C5—C6—C1	117.97 (11)	O3—C17—H17B	109.5
C5—C6—C7	124.27 (11)	H17A—C17—H17B	109.5
C1—C6—C7	117.67 (11)	O3—C17—H17C	109.5
N2—C7—N1	112.04 (10)	H17A—C17—H17C	109.5
N2—C7—C6	121.88 (11)	H17B—C17—H17C	109.5
N1—C7—C6	126.07 (11)	N1—C18—C19	110.49 (10)
N1—C8—C9	132.13 (11)	N1—C18—H18A	109.6
N1—C8—C13	105.44 (10)	C19—C18—H18A	109.6
C9—C8—C13	122.43 (11)	N1—C18—H18B	109.6
C10—C9—C8	116.70 (11)	C19—C18—H18B	109.6
C10—C9—H9A	121.7	H18A—C18—H18B	108.1
C8—C9—H9A	121.7	O4—C19—C18	111.58 (10)
C9—C10—C11	121.52 (12)	O4—C19—H19A	109.3
C9—C10—H10A	119.2	C18—C19—H19A	109.3
C11—C10—H10A	119.2	O4—C19—H19B	109.3
C12—C11—C10	121.19 (11)	C18—C19—H19B	109.3
C12—C11—C14	116.97 (11)	H19A—C19—H19B	108.0
C10—C11—C14	121.83 (11)	H5B—O5—H5C	107.1 (19)
C6—C1—C2—C3	0.6 (2)	N1—C8—C9—C10	179.73 (12)
C17—O3—C3—C4	9.95 (18)	C13—C8—C9—C10	−1.15 (17)
C17—O3—C3—C2	−170.04 (11)	C8—C9—C10—C11	0.95 (17)
C1—C2—C3—O3	178.34 (12)	C9—C10—C11—C12	0.34 (18)
C1—C2—C3—C4	−1.65 (19)	C9—C10—C11—C14	179.15 (11)
O3—C3—C4—C5	−179.16 (11)	C10—C11—C12—C13	−1.45 (17)
C2—C3—C4—C5	0.83 (19)	C14—C11—C12—C13	179.70 (10)
C3—C4—C5—C6	1.05 (18)	C7—N2—C13—C12	−179.60 (12)
C4—C5—C6—C1	−2.05 (18)	C7—N2—C13—C8	0.40 (13)
C4—C5—C6—C7	−178.52 (11)	C11—C12—C13—N2	−178.75 (11)
C2—C1—C6—C5	1.22 (18)	C11—C12—C13—C8	1.25 (16)
C2—C1—C6—C7	177.92 (11)	N1—C8—C13—N2	−0.62 (13)
C13—N2—C7—N1	−0.02 (13)	C9—C8—C13—N2	−179.95 (10)
C13—N2—C7—C6	178.74 (10)	N1—C8—C13—C12	179.38 (10)
C8—N1—C7—N2	−0.37 (13)	C9—C8—C13—C12	0.05 (17)
C18—N1—C7—N2	176.36 (11)	C15—O1—C14—O2	2.88 (18)
C8—N1—C7—C6	−179.06 (11)	C15—O1—C14—C11	−177.56 (10)
C18—N1—C7—C6	−2.33 (19)	C12—C11—C14—O2	12.75 (18)
C5—C6—C7—N2	147.34 (12)	C10—C11—C14—O2	−166.10 (12)
C1—C6—C7—N2	−29.13 (16)	C12—C11—C14—O1	−166.81 (10)
C5—C6—C7—N1	−34.09 (18)	C10—C11—C14—O1	14.34 (16)
C1—C6—C7—N1	149.44 (12)	C14—O1—C15—C16	−171.89 (13)
C7—N1—C8—C9	179.82 (12)	C7—N1—C18—C19	103.77 (13)
C18—N1—C8—C9	2.86 (19)	C8—N1—C18—C19	−79.98 (13)
C7—N1—C8—C13	0.59 (12)	N1—C18—C19—O4	−172.67 (10)
C18—N1—C8—C13	−176.38 (10)

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O4i	0.86 (2)	1.98 (2)	2.8165 (15)	165 (2)
O5—H5C···N2ii	0.85 (1)	1.95 (1)	2.8011 (15)	175 (2)
C15—H15A···Cg2iii	0.97	2.95	3.7247 (17)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯O4i	0.86 (2)	1.98 (2)	2.8165 (15)	165 (2)
O5—H5C⋯N2ii	0.85 (1)	1.95 (1)	2.8011 (15)	175 (2)
C15—H15A⋯Cg2iii	0.97	2.95	3.7247 (17)	138

Symmetry codes: (i) ; (ii) ; (iii) .