2-[(Quinolin-8-yl-oxy)meth-yl]-1H-benzimid-a-zole monohydrate.

In the title hydrate, C17H13N3O·H2O, the dihedral angle between the quinoline and benzimidazole ring systems is 6.22 (7)°. The water mol-ecule is linked to the main mol-ecule by N-H⋯O and O-H⋯N hydrogen bonds. Further O-H⋯N hydrogen bonds link the organic molecules into C(6) chains running parallel to the b axis.

Related literature

For background to the properties and applications of benz­imidazole and 8-hy­droxy­quinoline and their derivatives, see: Hanna & Moawad (2002 ▶); Patel & Patel (1999 ▶); Pierre et al. (2003 ▶); Liu et al. (2005 ▶); Wang et al. (2006 ▶); Wen et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H13N3O·H2O

M = 293.32

Orthorhombic,

a = 6.1679 (12) Å

b = 11.094 (2) Å

c = 20.502 (4) Å

V = 1402.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.12 × 0.10 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.989, T max = 0.994

10881 measured reflections

1947 independent reflections

1808 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.087

S = 1.06

1947 reflections

207 parameters

18 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813031322/bx2452sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031322/bx2452Isup2.hkl

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

C17H13N3O·H2O	F(000) = 616
Mr = 293.32	Dx = 1.389 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3957 reflections
a = 6.1679 (12) Å	θ = 3.0–27.9°
b = 11.094 (2) Å	µ = 0.09 mm−1
c = 20.502 (4) Å	T = 293 K
V = 1402.9 (5) Å3	Plate, colourless
Z = 4	0.12 × 0.10 × 0.06 mm

Bruker SMART CCD area-detector diffractometer	1947 independent reflections
Radiation source: fine-focus sealed tube	1808 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
phi and ω scans	θmax = 27.9°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.989, Tmax = 0.994	k = −14→13
10881 measured reflections	l = −20→26

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0385P)2 + 0.4303P] where P = (Fo2 + 2Fc2)/3
1947 reflections	(Δ/σ)max = 0.013
207 parameters	Δρmax = 0.20 e Å−3
18 restraints	Δρmin = −0.22 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	0.70538 (9)	0.86768 (5)	0.14109 (3)	0.01892 (14)
N1	0.82709 (12)	1.03042 (6)	0.05135 (3)	0.01977 (14)
N2	0.34077 (11)	0.92882 (6)	0.20550 (3)	0.01772 (16)
H2A	0.3746	0.9764	0.1740	0.021*
N3	0.36377 (12)	0.77363 (6)	0.27537 (3)	0.01932 (14)
C1	0.88756 (16)	1.10840 (7)	0.00577 (4)	0.0235 (2)
H1B	0.7980	1.1743	−0.0021	0.028*
C2	1.07849 (16)	1.09794 (8)	−0.03150 (4)	0.0242 (2)
H2B	1.1122	1.1549	−0.0632	0.029*
C3	1.21293 (15)	1.00257 (8)	−0.02022 (4)	0.0235 (2)
H3B	1.3415	0.9949	−0.0436	0.028*
C4	1.15598 (14)	0.91521 (7)	0.02721 (4)	0.01900 (19)
C5	1.28526 (14)	0.81205 (8)	0.03975 (4)	0.0201 (2)
H5A	1.4166	0.8017	0.0182	0.024*
C6	1.21598 (14)	0.72833 (7)	0.08357 (4)	0.0197 (2)
H6A	1.2990	0.6596	0.0907	0.024*
C7	1.01976 (13)	0.74376 (7)	0.11856 (4)	0.01837 (19)
H7A	0.9755	0.6855	0.1484	0.022*
C8	0.89491 (13)	0.84444 (7)	0.10856 (4)	0.01745 (19)
C9	0.95816 (14)	0.93301 (7)	0.06158 (4)	0.01845 (15)
C10	0.65019 (14)	0.78507 (7)	0.19152 (4)	0.01846 (19)
H10A	0.7684	0.7789	0.2225	0.022*
H10B	0.6240	0.7058	0.1732	0.022*
C11	0.45163 (14)	0.82967 (7)	0.22478 (4)	0.01850 (15)
C12	0.16288 (13)	0.93884 (7)	0.24609 (4)	0.01765 (19)
C13	−0.01106 (15)	1.01856 (7)	0.24679 (4)	0.0214 (2)
H13A	−0.0209	1.0820	0.2173	0.026*
C14	−0.16961 (15)	0.99854 (7)	0.29382 (4)	0.0239 (2)
H14A	−0.2892	1.0495	0.2956	0.029*
C15	−0.15352 (15)	0.90322 (8)	0.33867 (4)	0.0249 (2)
H15A	−0.2616	0.8931	0.3698	0.030*
C16	0.02011 (15)	0.82397 (8)	0.33743 (4)	0.0223 (2)
H16A	0.0301	0.7611	0.3673	0.027*
C17	0.17982 (14)	0.84134 (7)	0.28990 (4)	0.01820 (19)
O2	0.45798 (10)	1.11879 (5)	0.12375 (3)	0.02338 (15)
H2WA	0.5052 (13)	1.1686 (4)	0.1525 (2)	0.053 (3)*
H2WB	0.5604 (8)	1.0836 (5)	0.1021 (3)	0.047 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.0167 (3)	0.0218 (3)	0.0183 (2)	0.0025 (2)	0.0034 (2)	0.0034 (2)
N1	0.0224 (3)	0.0198 (2)	0.0171 (2)	0.0001 (2)	0.0005 (2)	−0.0011 (2)
N2	0.0172 (3)	0.0179 (3)	0.0180 (3)	−0.0017 (3)	0.0009 (3)	0.0006 (3)
N3	0.0177 (3)	0.0228 (2)	0.0175 (2)	−0.0019 (2)	0.0002 (2)	0.0011 (2)
C1	0.0309 (5)	0.0189 (3)	0.0207 (4)	0.0007 (4)	−0.0001 (4)	0.0000 (3)
C2	0.0298 (5)	0.0236 (4)	0.0192 (4)	−0.0066 (4)	0.0023 (3)	0.0007 (3)
C3	0.0238 (4)	0.0275 (4)	0.0191 (4)	−0.0059 (4)	0.0020 (4)	−0.0018 (3)
C4	0.0182 (4)	0.0230 (4)	0.0159 (3)	−0.0042 (4)	−0.0020 (3)	−0.0037 (3)
C5	0.0140 (4)	0.0289 (4)	0.0175 (3)	−0.0006 (4)	0.0003 (3)	−0.0048 (3)
C6	0.0179 (4)	0.0228 (4)	0.0184 (4)	0.0035 (4)	−0.0024 (3)	−0.0025 (3)
C7	0.0173 (4)	0.0208 (3)	0.0169 (3)	−0.0005 (3)	−0.0018 (3)	−0.0001 (3)
C8	0.0159 (4)	0.0210 (3)	0.0154 (3)	−0.0013 (3)	−0.0006 (3)	−0.0028 (3)
C9	0.0202 (3)	0.0185 (2)	0.0167 (3)	−0.0009 (2)	−0.0010 (3)	−0.0021 (2)
C10	0.0180 (4)	0.0189 (3)	0.0184 (3)	−0.0028 (4)	0.0023 (3)	0.0019 (3)
C11	0.0174 (3)	0.0211 (3)	0.0170 (3)	−0.0024 (3)	−0.0014 (2)	0.0000 (2)
C12	0.0164 (4)	0.0198 (3)	0.0168 (3)	−0.0039 (3)	0.0003 (3)	−0.0042 (3)
C13	0.0221 (4)	0.0188 (3)	0.0234 (4)	−0.0007 (4)	−0.0013 (3)	−0.0046 (3)
C14	0.0202 (4)	0.0244 (4)	0.0272 (4)	−0.0010 (4)	−0.0003 (4)	−0.0096 (3)
C15	0.0204 (4)	0.0338 (4)	0.0206 (4)	−0.0048 (4)	0.0046 (3)	−0.0091 (3)
C16	0.0209 (4)	0.0269 (4)	0.0190 (4)	−0.0046 (4)	0.0007 (3)	−0.0009 (3)
C17	0.0155 (4)	0.0215 (4)	0.0176 (3)	−0.0036 (3)	−0.0012 (3)	−0.0027 (3)
O2	0.0240 (3)	0.0216 (3)	0.0246 (3)	−0.0012 (3)	0.0020 (3)	−0.0029 (2)

O1—C8	1.3703 (10)	C6—H6A	0.9300
O1—C10	1.4230 (9)	C7—C8	1.3721 (11)
N1—C1	1.3268 (11)	C7—H7A	0.9300
N1—C9	1.3658 (11)	C8—C9	1.4303 (11)
N2—C11	1.3541 (11)	C10—C11	1.4864 (12)
N2—C12	1.3816 (11)	C10—H10A	0.9700
N2—H2A	0.8600	C10—H10B	0.9700
N3—C11	1.3253 (10)	C12—C13	1.3905 (12)
N3—C17	1.3930 (11)	C12—C17	1.4099 (11)
C1—C2	1.4087 (13)	C13—C14	1.3911 (13)
C1—H1B	0.9300	C13—H13A	0.9300
C2—C3	1.3640 (13)	C14—C15	1.4049 (12)
C2—H2B	0.9300	C14—H14A	0.9300
C3—C4	1.4172 (11)	C15—C16	1.3858 (13)
C3—H3B	0.9300	C15—H15A	0.9300
C4—C5	1.4183 (12)	C16—C17	1.3988 (12)
C4—C9	1.4227 (12)	C16—H16A	0.9300
C5—C6	1.3609 (11)	O2—H2WA	0.860 (5)
C5—H5A	0.9300	O2—H2WB	0.866 (5)
C6—C7	1.4173 (12)
C8—O1—C10	115.89 (6)	N1—C9—C8	119.05 (7)
C1—N1—C9	117.23 (8)	C4—C9—C8	118.17 (7)
C11—N2—C12	106.89 (6)	O1—C10—C11	108.42 (6)
C11—N2—H2A	126.6	O1—C10—H10A	110.0
C12—N2—H2A	126.6	C11—C10—H10A	110.0
C11—N3—C17	104.33 (7)	O1—C10—H10B	110.0
N1—C1—C2	124.28 (8)	C11—C10—H10B	110.0
N1—C1—H1B	117.9	H10A—C10—H10B	108.4
C2—C1—H1B	117.9	N3—C11—N2	113.77 (7)
C3—C2—C1	118.69 (8)	N3—C11—C10	122.66 (7)
C3—C2—H2B	120.7	N2—C11—C10	123.54 (7)
C1—C2—H2B	120.7	N2—C12—C13	132.08 (7)
C2—C3—C4	119.75 (8)	N2—C12—C17	105.26 (7)
C2—C3—H3B	120.1	C13—C12—C17	122.58 (8)
C4—C3—H3B	120.1	C12—C13—C14	116.62 (8)
C3—C4—C5	122.47 (8)	C12—C13—H13A	121.7
C3—C4—C9	117.22 (7)	C14—C13—H13A	121.7
C5—C4—C9	120.29 (7)	C13—C14—C15	121.61 (8)
C6—C5—C4	119.59 (8)	C13—C14—H14A	119.2
C6—C5—H5A	120.2	C15—C14—H14A	119.2
C4—C5—H5A	120.2	C16—C15—C14	121.34 (8)
C5—C6—C7	121.32 (8)	C16—C15—H15A	119.3
C5—C6—H6A	119.3	C14—C15—H15A	119.3
C7—C6—H6A	119.3	C15—C16—C17	118.01 (8)
C8—C7—C6	120.13 (7)	C15—C16—H16A	121.0
C8—C7—H7A	119.9	C17—C16—H16A	121.0
C6—C7—H7A	119.9	N3—C17—C16	130.41 (7)
O1—C8—C7	124.00 (7)	N3—C17—C12	109.74 (7)
O1—C8—C9	115.55 (7)	C16—C17—C12	119.82 (8)
C7—C8—C9	120.45 (7)	H2WA—O2—H2WB	113.3 (6)
N1—C9—C4	122.78 (7)
C9—N1—C1—C2	−1.10 (12)	C8—O1—C10—C11	175.34 (6)
N1—C1—C2—C3	−0.66 (13)	C17—N3—C11—N2	0.46 (9)
C1—C2—C3—C4	1.48 (12)	C17—N3—C11—C10	−177.96 (7)
C2—C3—C4—C5	177.95 (8)	C12—N2—C11—N3	−0.79 (9)
C2—C3—C4—C9	−0.58 (12)	C12—N2—C11—C10	177.61 (7)
C3—C4—C5—C6	−176.63 (8)	O1—C10—C11—N3	−177.95 (7)
C9—C4—C5—C6	1.85 (12)	O1—C10—C11—N2	3.80 (10)
C4—C5—C6—C7	−1.94 (12)	C11—N2—C12—C13	−176.09 (9)
C5—C6—C7—C8	0.15 (12)	C11—N2—C12—C17	0.74 (8)
C10—O1—C8—C7	5.26 (11)	N2—C12—C13—C14	177.02 (8)
C10—O1—C8—C9	−175.18 (7)	C17—C12—C13—C14	0.64 (12)
C6—C7—C8—O1	−178.74 (7)	C12—C13—C14—C15	0.56 (12)
C6—C7—C8—C9	1.72 (12)	C13—C14—C15—C16	−0.82 (13)
C1—N1—C9—C4	2.06 (11)	C14—C15—C16—C17	−0.15 (13)
C1—N1—C9—C8	−177.72 (7)	C11—N3—C17—C16	178.14 (9)
C3—C4—C9—N1	−1.25 (12)	C11—N3—C17—C12	0.05 (9)
C5—C4—C9—N1	−179.81 (7)	C15—C16—C17—N3	−176.62 (8)
C3—C4—C9—C8	178.52 (7)	C15—C16—C17—C12	1.31 (12)
C5—C4—C9—C8	−0.03 (11)	N2—C12—C17—N3	−0.50 (9)
O1—C8—C9—N1	−1.54 (11)	C13—C12—C17—N3	176.71 (7)
C7—C8—C9—N1	178.04 (7)	N2—C12—C17—C16	−178.82 (7)
O1—C8—C9—C4	178.67 (7)	C13—C12—C17—C16	−1.61 (12)
C7—C8—C9—C4	−1.75 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2WB···N1	0.87 (1)	2.03 (1)	2.8892 (10)	170 (1)
N2—H2A···O2	0.86	1.95	2.7880 (9)	163
O2—H2WA···N3i	0.86 (1)	2.05 (1)	2.9046 (9)	174 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2WB⋯N1	0.87 (1)	2.03 (1)	2.8892 (10)	170 (1)
N2—H2A⋯O2	0.86	1.95	2.7880 (9)	163
O2—H2WA⋯N3i	0.86 (1)	2.05 (1)	2.9046 (9)	174 (1)

Symmetry code: (i) .