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

Al-Douh, M.H.; Osman, H.; Hamid, S.A.; Kia, R.; Fun, H.-K.

doi:10.1107/S1600536809010769

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o913-o914

doi:10.1107/S1600536809010769

Open

access

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

Mohammed H. Al-Douh,^a Hasnah Osman,^a ‡ Shafida A. Hamid,^b Reza Kia ^c and Hoong-Kun Fun ^c ^*§

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bKulliyyah of Science, International Islamic University Malaysia (IIUM), Jalan Istana, Bandar Indera Mahkota 25200 Kuantan, Pahang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 20 March 2009; accepted 24 March 2009; online 28 March 2009)

The asymmetric unit of the title compound, C₂₂H₂₀N₂O₄·H₂O, comprises a substituted benzimidazole molecule and a water molecule 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 hydroxy-substituted benzene rings is 82.20 (5)°. In the crystal structure, intermolecular O—H⋯O hydrogen bonds, involving the hydroxy groups and water molecules, form R₄⁴(8) ring motifs, and link symmetry-related molecules into extended chains along the c axis. The crystal structure is further stabilized by weak intermolecular C—H⋯O hydrogen bonds, weak C—H⋯π and π–π stacking [centroid–centroid = 3.6495 (6)–3.7130 (6) Å] interactions. Intramolecular O—H⋯O and O—H⋯N interactions 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_r = 394.42
Triclinic, $[P \overline 1]$
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 (SADABS; 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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.133
S = 1.03
8009 reflections
274 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.33 e Å⁻³

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⋯O1W^iv	0.98	2.58	3.2762 (16)	128
C22—H22A⋯O3^v	0.98	2.54	3.2071 (14)	126
C22—H22B⋯Cg1^vi	0.98	2.80	3.5497 (13)	133
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) x, y-1, z; (iv) x, y, z-1; (v) x, y, z+1; (vi) -x+2, -y+2, -z+1. Cg1 is the centroid of the C15–C20 benzene ring.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Many benzimidazoles are pharmaceutical agents and are used widely in biological system applications which enable important synthetic strategies in drug discovery. Phenolic and anisolic benzimidazole derivatives have been synthesized and evaluated for vasodilator and antihypertensive activity (Soto et al., 2006), while other alkyloxyaryl benzimidazole derivatives have been tested for the spasmolytic activity (Vazquez et al., 2006). Latif et al. have developed the reactions of some phenolic aldehydes with o- phenylenediamine in great details and managed to isolate the title compound (Latif et al., 1983). In view of the above, we have obtained the title compound (I), derived from benzimidazole and a bis-Schiff base compound and have determined its crystsal structure herein.

The bond lengths and angles in (I) are consistent with those common to related reported structures (Elerman & Kabak, 1997; Liu et al., 2006). The molecular structure of (I) is shown in Fig. 1. Intramolecular O—H···O and O—H···N hydrogen bonds generate five and six membered rings with S(5) and S(6) ring motifs respectively (Bernstein et al., 1995). Intermolecular O—H···O hydrogen bonds, involving one of the hydroxy groups and one of the water molecules link neighbouring molecules into chains with R⁴₄(8) ring motifs (Bernstein et al., 1995). 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 hydroxy substituted benzene rings is 82.20 (5)°. In the crystal structure the molecules are linked together by four-membered O—H···O—H···O—H interactions into 1-D extended chains along the c axis. The crystal structure is further stabilized by intermolecular C—H···O hydrogen bonds, weak intermolecular C—H···π (Table 1; Cg1 is the centroids of the C15–C20 benzene ring), and π-π interactions [Cg2···Cg2^vii = 3.6495 (6) Å; Cg3 ···Cg4^vii = 3.7130 (6) Å; Cg2, Cg3 and Cg4 are the centroids of the N1/C7/N2/C8/C13, C1–C6 and C8–C13 rings].

Related literature top

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); 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). Cg1 is the centroid of the C15–C20 benzene ring.

Experimental top

The synthetic method has been described earlier (Al-Douh et al., 2006, 2007), while the single crystals suitable for X-ray diffraction were obtained by evaporation of a methanol solution of (I) at 353 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. Intramolecular H bonds are drawn as a dashed line.
	Fig. 2. Part of the crystal structure of the title compound, viewed along the a-axis showing 1-D extended chains along the c-axis. Intermolecular interactions are drawn as dashed lines.

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

Crystal data top

C₂₂H₂₀N₂O₄·H₂O	Z = 2
M_r = 394.42	F(000) = 416
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.049	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(F_o²) + (0.0658P)² + 0.2927P] where P = (F_o² + 2F_c²)/3
8009 reflections	(Δ/σ)_max = 0.001
274 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₂H₂₀N₂O₄·H₂O	γ = 97.993 (1)°
M_r = 394.42	V = 916.18 (2) Å³
Triclinic, P1	Z = 2
a = 7.5076 (1) Å	Mo Kα radiation
b = 9.8557 (1) Å	µ = 0.10 mm⁻¹
c = 13.2240 (2) Å	T = 100 K
α = 106.306 (1)°	0.48 × 0.28 × 0.10 mm
β = 97.135 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8009 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	6304 reflections with I > 2˘I)
T_min = 0.952, T_max = 0.990	R_int = 0.030
33715 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.58 e Å⁻³
8009 reflections	Δρ_min = −0.33 e Å⁻³
274 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1W^iv	0.98	2.58	3.2762 (16)	128
C22—H22A···O3^v	0.98	2.54	3.2071 (14)	126
C22—H22B···Cg1^vi	0.98	2.80	3.5497 (13)	133

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀N₂O₄·H₂O
M_r	394.42
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.5076 (1), 9.8557 (1), 13.2240 (2)
α, β, γ (°)	106.306 (1), 97.135 (1), 97.993 (1)
V (Å³)	916.18 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.48 × 0.28 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.952, 0.990
No. of measured, independent and observed [I > 2˘I)] reflections	33715, 8009, 6304
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.133, 1.03
No. of reflections	8009
No. of parameters	274
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.33

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
O1—H1···N1	0.8400	1.8000	2.5447 (12)	147.00
O1W—H2W1···O1ⁱ	0.84 (2)	2.23 (2)	3.0151 (11)	155 (2)
O2—H2···O4	0.8400	2.2100	2.6650 (11)	114.00
O2—H2···O1Wⁱⁱ	0.8400	1.9500	2.7401 (11)	155.00
O1W—H1W1···O2ⁱⁱⁱ	0.87 (2)	2.04 (2)	2.8987 (12)	168.5 (19)
C21—H21B···O1W^iv	0.9800	2.5800	3.2762 (16)	128.00
C22—H22A···O3^v	0.9800	2.5400	3.2071 (14)	126.00
C22—H22B···Cg1^vi	0.98	2.80	3.5497 (13)	133

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

Footnotes

‡Additional corresponding author, e-mail: ohasnah@usm.my.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

We thank the Malaysian Government and Universiti Sains Malaysia (USM) for an FRGS grant [304/PKIMIA/638122] to conduct this work. MHA-D thanks the Yemeni Government and Hadhramout University of Science and Technology (HUST) for financial scholarship support. HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Al-Douh, M. H., Hamid, S. A., Osman, H., Ng, S.-L. & Fun, H.-K. (2006). Acta Cryst. E62, o3954–o3956. Web of Science CSD CrossRef IUCr Journals Google Scholar
Al-Douh, M. H., Hamid, S. A., Osman, H., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o3570–o3571. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). 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
Elerman, Y. & Kabak, M. (1997). Acta Cryst. C53, 372–374. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Latif, N., Mishriky, N. & F. M. Assad (1983). Recl Trav. Chim Pays-Bas, 102, 73–77. Google Scholar
Liu, Y.-F., Xia, H.-T., Yang, S.-P. & Wang, D.-Q. (2006). Acta Cryst. E62, o5908–o5909. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soto, S. E., Molina, R. V., Crespo, F. A., Galicia, J. V., Diaz, H. M., Piedra, M. T. & Vazquez, G. N. (2006). Life Sci. 79, 430–435. Web of Science PubMed Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vazquez, G. N., Diaz, H. M., Crespo, F. A., Rivera, I. L., Molina, R. V., Muniz, O. M. & Soto, S. E. (2006). Bioorg. Med. Chem. Lett. 16, 4169–4173. Web of Science PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o913-o914

doi:10.1107/S1600536809010769

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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