2-[1-(2-Hydroxy-3-methoxybenzyl)-1H-benzimidazol-2-yl]-6-methoxyphenol monohydrate.

The asymmetric unit of the title compound, C(22)H(20)N(2)O(4)·H(2)O, comprises a substituted benzimidazole molecule and a water mol-ecule of crystallization. The dihedral angles between the benzimidazole ring system and the two outer benzene rings are 16.54 (4) and 86.13 (4)°. The dihedral angle between the two hydr-oxy-substituted benzene rings is 82.20 (5)°. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds, involving the hydr-oxy groups and water mol-ecules, form R(4) (4)(8) ring motifs, and link symmetry-related mol-ecules into extended chains along the c axis. The crystal structure is further stabilized by weak inter-molecular C-H⋯O hydrogen bonds, weak C-H⋯π and π-π stacking [centroid-centroid = 3.6495 (6)-3.7130 (6) Å] inter-actions. Intra-molecular O-H⋯O and O-H⋯N inter-actions are also present.

Related literature

For hydrogen-bond motifs, see Bernstein et al. (1995 ▶). For the synthesis and bioactivity of benzimidazoles see, for example: Soto et al. (2006 ▶); Vazquez et al. (2006 ▶); Latif et al. (1983 ▶). For related structures, see: Elerman & Kabak (1997 ▶); Liu et al. (2006 ▶); Al-Douh et al. (2006 ▶, 2007 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H20N2O4·H2O

M = 394.42

Triclinic,

a = 7.5076 (1) Å

b = 9.8557 (1) Å

c = 13.2240 (2) Å

α = 106.306 (1)°

β = 97.135 (1)°

γ = 97.993 (1)°

V = 916.18 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.48 × 0.28 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.952, T max = 0.990

33715 measured reflections

8009 independent reflections

6304 reflections with I > 2˘I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.133

S = 1.03

8009 reflections

274 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.58 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010769/lh2793sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010769/lh2793Isup2.hkl

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

C22H20N2O4·H2O	Z = 2
Mr = 394.42	F(000) = 416
Triclinic, P1	Dx = 1.430 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5076 (1) Å	Cell parameters from 9908 reflections
b = 9.8557 (1) Å	θ = 2.5–33.4°
c = 13.2240 (2) Å	µ = 0.10 mm−1
α = 106.306 (1)°	T = 100 K
β = 97.135 (1)°	Plate, colourless
γ = 97.993 (1)°	0.48 × 0.28 × 0.10 mm
V = 916.18 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	8009 independent reflections
Radiation source: fine-focus sealed tube	6304 reflections with I > 2˘I)
graphite	Rint = 0.030
φ and ω scans	θmax = 35.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→12
Tmin = 0.952, Tmax = 0.990	k = −15→15
33715 measured reflections	l = −21→21

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0658P)2 + 0.2927P] where P = (Fo2 + 2Fc2)/3
8009 reflections	(Δ/σ)max = 0.001
274 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.70651 (10)	0.86574 (8)	−0.22860 (6)	0.01748 (14)
H1	0.7410	0.9452	−0.1807	0.026*
O2	0.57454 (9)	0.84985 (8)	0.36393 (6)	0.01561 (13)
H2	0.5792	0.8439	0.4263	0.023*
O3	0.65167 (12)	0.60902 (8)	−0.35747 (6)	0.02243 (16)
O4	0.83510 (10)	0.78670 (9)	0.48995 (6)	0.01926 (15)
N1	0.78166 (11)	1.04082 (9)	−0.04007 (7)	0.01479 (14)
N2	0.68948 (10)	0.98309 (9)	0.09978 (6)	0.01414 (14)
C1	0.68617 (12)	0.75865 (10)	−0.18267 (7)	0.01435 (16)
C2	0.65860 (13)	0.61781 (11)	−0.25179 (8)	0.01672 (17)
C3	0.63781 (14)	0.50113 (11)	−0.21256 (9)	0.01892 (18)
H3A	0.6186	0.4059	−0.2598	0.023*
C4	0.64553 (14)	0.52522 (11)	−0.10278 (9)	0.01897 (18)
H4A	0.6326	0.4457	−0.0753	0.023*
C5	0.67176 (13)	0.66317 (11)	−0.03354 (8)	0.01655 (17)
H5A	0.6777	0.6774	0.0410	0.020*
C6	0.68979 (12)	0.78324 (10)	−0.07211 (7)	0.01388 (15)
C7	0.71903 (12)	0.93282 (10)	−0.00369 (7)	0.01363 (15)
C8	0.74228 (12)	1.13195 (10)	0.13166 (8)	0.01435 (15)
C9	0.74225 (13)	1.23678 (11)	0.22774 (8)	0.01755 (17)
H9A	0.7034	1.2126	0.2872	0.021*
C10	0.80202 (14)	1.37822 (12)	0.23185 (9)	0.02025 (18)
H10A	0.8038	1.4529	0.2958	0.024*
C11	0.86028 (14)	1.41416 (11)	0.14373 (9)	0.02055 (19)
H11A	0.9011	1.5122	0.1498	0.025*
C12	0.85915 (13)	1.30930 (11)	0.04864 (8)	0.01792 (17)
H12A	0.8982	1.3335	−0.0107	0.022*
C13	0.79834 (12)	1.16605 (10)	0.04318 (8)	0.01454 (16)
C14	0.62110 (12)	0.90630 (11)	0.17087 (7)	0.01496 (16)
H14A	0.5363	0.8169	0.1275	0.018*
H14B	0.5515	0.9667	0.2183	0.018*
C15	0.77308 (12)	0.86831 (10)	0.23893 (7)	0.01369 (15)
C16	0.74231 (12)	0.84165 (10)	0.33383 (7)	0.01303 (15)
C17	0.88347 (12)	0.81141 (10)	0.39986 (7)	0.01459 (16)
C18	1.05599 (13)	0.81031 (11)	0.37185 (8)	0.01720 (17)
H18A	1.1524	0.7925	0.4173	0.021*
C19	1.08576 (13)	0.83566 (11)	0.27609 (8)	0.01798 (17)
H19A	1.2026	0.8336	0.2558	0.022*
C20	0.94569 (12)	0.86386 (11)	0.21028 (8)	0.01622 (17)
H20A	0.9675	0.8803	0.1451	0.019*
C21	0.6815 (2)	0.47733 (14)	−0.42586 (10)	0.0353 (3)
H21A	0.6958	0.4884	−0.4959	0.053*
H21B	0.5768	0.4012	−0.4344	0.053*
H21C	0.7923	0.4517	−0.3944	0.053*
C22	0.97989 (14)	0.78394 (12)	0.57027 (8)	0.02013 (19)
H22A	0.9313	0.7807	0.6352	0.030*
H22B	1.0733	0.8706	0.5866	0.030*
H22C	1.0342	0.6986	0.5441	0.030*
O1W	0.50926 (11)	0.14161 (9)	0.43879 (6)	0.02107 (15)
H2W1	0.433 (3)	0.158 (2)	0.3932 (17)	0.055 (6)*
H1W1	0.515 (3)	0.052 (2)	0.4097 (15)	0.043 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0253 (3)	0.0151 (3)	0.0131 (3)	0.0034 (3)	0.0034 (2)	0.0061 (2)
O2	0.0147 (3)	0.0218 (3)	0.0125 (3)	0.0045 (2)	0.0046 (2)	0.0073 (3)
O3	0.0351 (4)	0.0180 (3)	0.0133 (3)	0.0056 (3)	0.0046 (3)	0.0028 (3)
O4	0.0175 (3)	0.0300 (4)	0.0152 (3)	0.0056 (3)	0.0030 (2)	0.0138 (3)
N1	0.0164 (3)	0.0157 (4)	0.0143 (3)	0.0041 (3)	0.0039 (3)	0.0066 (3)
N2	0.0152 (3)	0.0165 (4)	0.0123 (3)	0.0033 (3)	0.0033 (2)	0.0063 (3)
C1	0.0154 (3)	0.0157 (4)	0.0138 (4)	0.0040 (3)	0.0030 (3)	0.0066 (3)
C2	0.0196 (4)	0.0177 (4)	0.0135 (4)	0.0047 (3)	0.0033 (3)	0.0048 (3)
C3	0.0217 (4)	0.0151 (4)	0.0195 (5)	0.0035 (3)	0.0029 (3)	0.0046 (3)
C4	0.0207 (4)	0.0164 (4)	0.0219 (5)	0.0033 (3)	0.0032 (3)	0.0095 (4)
C5	0.0178 (4)	0.0183 (4)	0.0158 (4)	0.0036 (3)	0.0033 (3)	0.0085 (3)
C6	0.0138 (3)	0.0156 (4)	0.0134 (4)	0.0035 (3)	0.0025 (3)	0.0058 (3)
C7	0.0139 (3)	0.0161 (4)	0.0121 (4)	0.0038 (3)	0.0024 (3)	0.0056 (3)
C8	0.0138 (3)	0.0169 (4)	0.0134 (4)	0.0039 (3)	0.0018 (3)	0.0058 (3)
C9	0.0168 (4)	0.0212 (4)	0.0139 (4)	0.0047 (3)	0.0017 (3)	0.0039 (3)
C10	0.0207 (4)	0.0197 (5)	0.0184 (4)	0.0051 (3)	0.0018 (3)	0.0025 (4)
C11	0.0217 (4)	0.0168 (4)	0.0226 (5)	0.0042 (3)	0.0024 (3)	0.0053 (4)
C12	0.0189 (4)	0.0170 (4)	0.0196 (4)	0.0040 (3)	0.0039 (3)	0.0078 (3)
C13	0.0145 (3)	0.0165 (4)	0.0139 (4)	0.0039 (3)	0.0026 (3)	0.0062 (3)
C14	0.0142 (3)	0.0203 (4)	0.0131 (4)	0.0037 (3)	0.0035 (3)	0.0086 (3)
C15	0.0139 (3)	0.0165 (4)	0.0117 (4)	0.0034 (3)	0.0026 (3)	0.0054 (3)
C16	0.0129 (3)	0.0150 (4)	0.0115 (4)	0.0026 (3)	0.0026 (3)	0.0043 (3)
C17	0.0158 (3)	0.0165 (4)	0.0128 (4)	0.0030 (3)	0.0021 (3)	0.0067 (3)
C18	0.0153 (4)	0.0206 (4)	0.0182 (4)	0.0048 (3)	0.0022 (3)	0.0095 (4)
C19	0.0144 (4)	0.0230 (5)	0.0195 (4)	0.0053 (3)	0.0044 (3)	0.0097 (4)
C20	0.0148 (3)	0.0214 (4)	0.0148 (4)	0.0045 (3)	0.0045 (3)	0.0078 (3)
C21	0.0633 (9)	0.0230 (6)	0.0184 (5)	0.0126 (6)	0.0104 (5)	0.0008 (4)
C22	0.0206 (4)	0.0265 (5)	0.0146 (4)	0.0048 (3)	−0.0004 (3)	0.0095 (4)
O1W	0.0267 (4)	0.0235 (4)	0.0158 (3)	0.0093 (3)	0.0049 (3)	0.0076 (3)

O1—C1	1.3581 (11)	C10—C11	1.4107 (16)
O1—H1	0.8400	C10—H10A	0.9500
O2—C16	1.3734 (11)	C11—C12	1.3837 (15)
O2—H2	0.8400	C11—H11A	0.9500
O3—C2	1.3697 (12)	C12—C13	1.4008 (14)
O3—C21	1.4229 (14)	C12—H12A	0.9500
O4—C17	1.3624 (11)	C14—C15	1.5183 (12)
O4—C22	1.4312 (12)	C14—H14A	0.9900
N1—C7	1.3379 (12)	C14—H14B	0.9900
N1—C13	1.3824 (13)	C15—C16	1.3920 (13)
N2—C7	1.3757 (12)	C15—C20	1.3976 (12)
N2—C8	1.3917 (12)	C16—C17	1.4066 (12)
N2—C14	1.4599 (12)	C17—C18	1.3913 (13)
C1—C2	1.4021 (14)	C18—C19	1.3959 (14)
C1—C6	1.4094 (13)	C18—H18A	0.9500
C2—C3	1.3860 (14)	C19—C20	1.3893 (13)
C3—C4	1.3961 (15)	C19—H19A	0.9500
C3—H3A	0.9500	C20—H20A	0.9500
C4—C5	1.3810 (15)	C21—H21A	0.9800
C4—H4A	0.9500	C21—H21B	0.9800
C5—C6	1.4108 (13)	C21—H21C	0.9800
C5—H5A	0.9500	C22—H22A	0.9800
C6—C7	1.4669 (13)	C22—H22B	0.9800
C8—C9	1.3945 (14)	C22—H22C	0.9800
C8—C13	1.4010 (13)	O1W—H2W1	0.84 (2)
C9—C10	1.3874 (15)	O1W—H1W1	0.87 (2)
C9—H9A	0.9500
C1—O1—H1	109.5	C11—C12—H12A	121.2
C16—O2—H2	109.5	C13—C12—H12A	121.2
C2—O3—C21	116.18 (9)	N1—C13—C12	130.25 (9)
C17—O4—C22	116.88 (8)	N1—C13—C8	109.19 (8)
C7—N1—C13	106.48 (8)	C12—C13—C8	120.56 (9)
C7—N2—C8	106.87 (8)	N2—C14—C15	112.59 (7)
C7—N2—C14	130.73 (8)	N2—C14—H14A	109.1
C8—N2—C14	122.38 (8)	C15—C14—H14A	109.1
O1—C1—C2	116.37 (8)	N2—C14—H14B	109.1
O1—C1—C6	123.45 (9)	C15—C14—H14B	109.1
C2—C1—C6	120.18 (8)	H14A—C14—H14B	107.8
O3—C2—C3	125.03 (9)	C16—C15—C20	118.99 (8)
O3—C2—C1	114.20 (8)	C16—C15—C14	119.49 (8)
C3—C2—C1	120.76 (9)	C20—C15—C14	121.49 (8)
C2—C3—C4	119.20 (9)	O2—C16—C15	119.26 (8)
C2—C3—H3A	120.4	O2—C16—C17	120.41 (8)
C4—C3—H3A	120.4	C15—C16—C17	120.29 (8)
C5—C4—C3	120.85 (9)	O4—C17—C18	125.31 (8)
C5—C4—H4A	119.6	O4—C17—C16	114.37 (8)
C3—C4—H4A	119.6	C18—C17—C16	120.31 (8)
C4—C5—C6	120.82 (9)	C17—C18—C19	119.19 (8)
C4—C5—H5A	119.6	C17—C18—H18A	120.4
C6—C5—H5A	119.6	C19—C18—H18A	120.4
C1—C6—C5	118.16 (9)	C20—C19—C18	120.45 (9)
C1—C6—C7	117.77 (8)	C20—C19—H19A	119.8
C5—C6—C7	124.03 (8)	C18—C19—H19A	119.8
N1—C7—N2	111.35 (8)	C19—C20—C15	120.73 (9)
N1—C7—C6	120.54 (8)	C19—C20—H20A	119.6
N2—C7—C6	128.11 (8)	C15—C20—H20A	119.6
N2—C8—C9	131.51 (9)	O3—C21—H21A	109.5
N2—C8—C13	106.08 (8)	O3—C21—H21B	109.5
C9—C8—C13	122.40 (9)	H21A—C21—H21B	109.5
C10—C9—C8	116.42 (9)	O3—C21—H21C	109.5
C10—C9—H9A	121.8	H21A—C21—H21C	109.5
C8—C9—H9A	121.8	H21B—C21—H21C	109.5
C9—C10—C11	121.84 (10)	O4—C22—H22A	109.5
C9—C10—H10A	119.1	O4—C22—H22B	109.5
C11—C10—H10A	119.1	H22A—C22—H22B	109.5
C12—C11—C10	121.25 (10)	O4—C22—H22C	109.5
C12—C11—H11A	119.4	H22A—C22—H22C	109.5
C10—C11—H11A	119.4	H22B—C22—H22C	109.5
C11—C12—C13	117.52 (9)	H2W1—O1W—H1W1	103.0 (18)
C21—O3—C2—C3	−20.13 (15)	C8—C9—C10—C11	−0.19 (14)
C21—O3—C2—C1	160.96 (10)	C9—C10—C11—C12	0.43 (16)
O1—C1—C2—O3	−1.55 (12)	C10—C11—C12—C13	−0.13 (15)
C6—C1—C2—O3	177.80 (8)	C7—N1—C13—C12	179.37 (10)
O1—C1—C2—C3	179.48 (9)	C7—N1—C13—C8	−0.59 (10)
C6—C1—C2—C3	−1.16 (14)	C11—C12—C13—N1	179.66 (9)
O3—C2—C3—C4	−179.16 (9)	C11—C12—C13—C8	−0.39 (14)
C1—C2—C3—C4	−0.31 (15)	N2—C8—C13—N1	−0.56 (10)
C2—C3—C4—C5	0.61 (15)	C9—C8—C13—N1	−179.40 (8)
C3—C4—C5—C6	0.58 (14)	N2—C8—C13—C12	179.47 (8)
O1—C1—C6—C5	−178.40 (8)	C9—C8—C13—C12	0.64 (14)
C2—C1—C6—C5	2.28 (13)	C7—N2—C14—C15	91.13 (11)
O1—C1—C6—C7	−0.65 (13)	C8—N2—C14—C15	−87.41 (10)
C2—C1—C6—C7	−179.96 (8)	N2—C14—C15—C16	157.87 (9)
C4—C5—C6—C1	−2.01 (13)	N2—C14—C15—C20	−20.07 (13)
C4—C5—C6—C7	−179.61 (9)	C20—C15—C16—O2	178.18 (9)
C13—N1—C7—N2	1.57 (10)	C14—C15—C16—O2	0.19 (13)
C13—N1—C7—C6	−178.56 (8)	C20—C15—C16—C17	0.30 (14)
C8—N2—C7—N1	−1.94 (10)	C14—C15—C16—C17	−177.69 (9)
C14—N2—C7—N1	179.36 (8)	C22—O4—C17—C18	11.29 (15)
C8—N2—C7—C6	178.21 (8)	C22—O4—C17—C16	−167.85 (9)
C14—N2—C7—C6	−0.50 (15)	O2—C16—C17—O4	2.44 (13)
C1—C6—C7—N1	−15.16 (12)	C15—C16—C17—O4	−179.70 (9)
C5—C6—C7—N1	162.45 (9)	O2—C16—C17—C18	−176.74 (9)
C1—C6—C7—N2	164.69 (9)	C15—C16—C17—C18	1.11 (15)
C5—C6—C7—N2	−17.71 (14)	O4—C17—C18—C19	179.16 (10)
C7—N2—C8—C9	−179.84 (9)	C16—C17—C18—C19	−1.75 (15)
C14—N2—C8—C9	−1.00 (15)	C17—C18—C19—C20	0.99 (16)
C7—N2—C8—C13	1.47 (9)	C18—C19—C20—C15	0.42 (16)
C14—N2—C8—C13	−179.69 (8)	C16—C15—C20—C19	−1.06 (15)
N2—C8—C9—C10	−178.84 (9)	C14—C15—C20—C19	176.89 (9)
C13—C8—C9—C10	−0.33 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.80	2.5447 (12)	147
O1W—H2W1···O1i	0.84 (2)	2.23 (2)	3.0151 (11)	155 (2)
O2—H2···O4	0.84	2.21	2.6650 (11)	114
O2—H2···O1Wii	0.84	1.95	2.7401 (11)	155
O1W—H1W1···O2iii	0.87 (2)	2.04 (2)	2.8987 (12)	168.5 (19)
C21—H21B···O1Wiv	0.98	2.58	3.2762 (16)	128
C22—H22A···O3v	0.98	2.54	3.2071 (14)	126
C22—H22B···Cg1vi	0.98	2.80	3.5497 (13)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.80	2.5447 (12)	147
O1W—H2W1⋯O1i	0.84 (2)	2.23 (2)	3.0151 (11)	155 (2)
O2—H2⋯O4	0.84	2.21	2.6650 (11)	114
O2—H2⋯O1Wii	0.84	1.95	2.7401 (11)	155
O1W—H1W1⋯O2iii	0.87 (2)	2.04 (2)	2.8987 (12)	168.5 (19)
C21—H21B⋯O1Wiv	0.98	2.58	3.2762 (16)	128
C22—H22A⋯O3v	0.98	2.54	3.2071 (14)	126
C22—H22B⋯Cg1vi	0.98	2.80	3.5497 (13)	133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg1 is the centroid of the C15–C20 benzene ring.