2-({4-[4-(1H-Benzimidazol-2-yl)phen-yl]-1H-1,2,3-triazol-1-yl}meth-oxy)ethanol.

In the title molecule, C(18)H(17)N(5)O(2), the dihedral angle between the benzene plane and the benzimidazole plane is 19.8 (1)° and the angle between the benzene plane and the triazole plane is 16.7 (1)°. In the crystal, mol-ecules are connected by O-H⋯N hydrogen bonds, forming zigzag chains along the c-axis direction. The chains are connected by bifurcated N-H⋯(N,N) hydrogen bonds into layers parallel to (100). These layers are connected along the a-axis direction by weak C-H⋯O contacts, forming a three-dimensional network.

Related literature

For the bioactivity of benzimidazoles, see: Tebbe et al. (1997 ▶); Andrzejewska et al. (2002 ▶); Navarrete-Vázquez et al. (2003 ▶); Terzioglu et al. (2004 ▶); Özden et al. (2005 ▶). For the bioactivity of 1,2,3-triazoles, see: Chen et al. (2000 ▶); Manfredini et al. (2000 ▶). For the synthetic methods, see: Huisgen (1963 ▶); Crisp & Flynn (1993 ▶); Wu et al. (2004 ▶); Navarrete-Vázquez et al. (2007 ▶); Krim et al. (2009 ▶).

Experimental

Crystal data

C18H17N5O2

M = 335.37

Monoclinic,

a = 10.4449 (5) Å

b = 7.7754 (4) Å

c = 20.2119 (10) Å

β = 99.354 (1)°

V = 1619.65 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 170 K

0.40 × 0.32 × 0.11 mm

Data collection

Siemens SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.953, T max = 0.990

15768 measured reflections

3295 independent reflections

2562 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.102

S = 1.14

3295 reflections

235 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Siemens, 1995 ▶); cell refinement: SAINT (Siemens, 1995 ▶); 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) global, I. DOI: 10.1107/S1600536812023410/nc2282sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023410/nc2282Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023410/nc2282Isup3.cml

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

C18H17N5O2	F(000) = 704
Mr = 335.37	Dx = 1.375 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8027 reflections
a = 10.4449 (5) Å	θ = 3–24°
b = 7.7754 (4) Å	µ = 0.09 mm−1
c = 20.2119 (10) Å	T = 170 K
β = 99.354 (1)°	Block, yellow
V = 1619.65 (14) Å3	0.40 × 0.32 × 0.11 mm
Z = 4

Siemens SMART 1K CCD diffractometer	3295 independent reflections
Radiation source: normal-focus sealed tube	2562 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ω scans	θmax = 26.8°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −13→13
Tmin = 0.953, Tmax = 0.990	k = −9→9
15768 measured reflections	l = −25→25

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.023P)2 + 0.6P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.001
3295 reflections	Δρmax = 0.20 e Å−3
235 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0056 (7)

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	0.50237 (13)	0.39456 (17)	0.71767 (6)	0.0308 (3)
O2	0.67189 (14)	0.21899 (18)	0.87378 (7)	0.0335 (4)
N1	1.07016 (15)	0.9376 (2)	0.37941 (8)	0.0265 (4)
N2	0.91403 (15)	1.1341 (2)	0.37934 (8)	0.0277 (4)
N3	0.56182 (15)	0.3846 (2)	0.60950 (7)	0.0272 (4)
N4	0.65832 (16)	0.2730 (2)	0.60375 (8)	0.0350 (4)
N5	0.73569 (16)	0.3493 (2)	0.56742 (8)	0.0331 (4)
C1	0.95442 (18)	0.9778 (2)	0.39886 (9)	0.0252 (4)
C2	1.10804 (18)	1.0777 (2)	0.34516 (9)	0.0265 (4)
C3	1.21525 (18)	1.1085 (3)	0.31418 (10)	0.0317 (5)
H3A	1.2823	1.0256	0.3148	0.038*
C4	1.2198 (2)	1.2654 (3)	0.28242 (10)	0.0350 (5)
H4A	1.2918	1.2912	0.2608	0.042*
C5	1.12061 (19)	1.3873 (3)	0.28139 (10)	0.0343 (5)
H5A	1.1267	1.4936	0.2589	0.041*
C6	1.01424 (19)	1.3565 (3)	0.31228 (9)	0.0310 (5)
H6A	0.9471	1.4393	0.3112	0.037*
C7	1.00880 (17)	1.1996 (2)	0.34504 (9)	0.0257 (4)
C8	0.88408 (17)	0.8577 (2)	0.43576 (9)	0.0253 (4)
C9	0.91089 (18)	0.6817 (2)	0.43692 (9)	0.0283 (5)
H9A	0.9749	0.6389	0.4127	0.034*
C10	0.84603 (18)	0.5686 (2)	0.47263 (9)	0.0268 (4)
H10A	0.8647	0.4491	0.4721	0.032*
C11	0.75345 (18)	0.6289 (2)	0.50939 (9)	0.0258 (4)
C12	0.72431 (18)	0.8045 (3)	0.50722 (9)	0.0288 (5)
H12A	0.6595	0.8469	0.5310	0.035*
C13	0.78828 (18)	0.9175 (3)	0.47105 (9)	0.0289 (5)
H13A	0.7671	1.0364	0.4701	0.035*
C14	0.68875 (18)	0.5107 (2)	0.55019 (9)	0.0256 (4)
C15	0.57733 (18)	0.5326 (2)	0.57719 (9)	0.0265 (4)
H15A	0.5229	0.6312	0.5738	0.032*
C16	0.46450 (19)	0.3426 (3)	0.65116 (9)	0.0302 (5)
H16A	0.3817	0.3995	0.6326	0.036*
H16B	0.4495	0.2168	0.6499	0.036*
C17	0.59651 (18)	0.2857 (2)	0.75702 (9)	0.0288 (4)
H17A	0.6829	0.3018	0.7438	0.035*
H17B	0.5713	0.1634	0.7505	0.035*
C18	0.59977 (19)	0.3374 (3)	0.82907 (10)	0.0334 (5)
H18A	0.6391	0.4531	0.8364	0.040*
H18B	0.5099	0.3439	0.8387	0.040*
H1A	1.118 (2)	0.846 (3)	0.3930 (10)	0.040 (6)*
H2A	0.756 (3)	0.258 (3)	0.8779 (12)	0.068 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0328 (8)	0.0313 (8)	0.0286 (7)	0.0077 (6)	0.0061 (6)	0.0048 (6)
O2	0.0256 (8)	0.0346 (8)	0.0382 (8)	−0.0039 (7)	−0.0008 (6)	0.0083 (6)
N1	0.0222 (9)	0.0261 (9)	0.0313 (9)	0.0041 (7)	0.0043 (7)	0.0013 (7)
N2	0.0257 (9)	0.0280 (9)	0.0289 (9)	0.0042 (7)	0.0026 (7)	−0.0002 (7)
N3	0.0248 (9)	0.0285 (9)	0.0286 (9)	0.0033 (7)	0.0053 (7)	0.0029 (7)
N4	0.0326 (10)	0.0313 (10)	0.0427 (10)	0.0087 (8)	0.0114 (8)	0.0057 (8)
N5	0.0304 (9)	0.0340 (10)	0.0362 (9)	0.0060 (8)	0.0096 (8)	0.0050 (8)
C1	0.0226 (10)	0.0288 (11)	0.0234 (10)	0.0030 (8)	0.0015 (8)	−0.0039 (8)
C2	0.0250 (10)	0.0266 (10)	0.0267 (10)	0.0009 (8)	0.0002 (8)	−0.0009 (8)
C3	0.0246 (11)	0.0352 (12)	0.0357 (11)	0.0023 (9)	0.0063 (9)	−0.0009 (9)
C4	0.0291 (11)	0.0408 (13)	0.0358 (11)	−0.0034 (10)	0.0073 (9)	0.0024 (9)
C5	0.0342 (12)	0.0337 (12)	0.0334 (11)	−0.0038 (10)	0.0003 (9)	0.0079 (9)
C6	0.0292 (11)	0.0302 (11)	0.0316 (11)	0.0036 (9)	−0.0007 (9)	0.0012 (9)
C7	0.0224 (10)	0.0289 (11)	0.0251 (10)	−0.0009 (8)	0.0017 (8)	−0.0018 (8)
C8	0.0226 (10)	0.0296 (11)	0.0225 (9)	0.0023 (8)	0.0000 (8)	−0.0002 (8)
C9	0.0222 (10)	0.0340 (12)	0.0287 (10)	0.0040 (9)	0.0041 (8)	−0.0043 (9)
C10	0.0244 (10)	0.0265 (10)	0.0289 (10)	0.0029 (8)	0.0020 (8)	−0.0011 (8)
C11	0.0233 (10)	0.0315 (11)	0.0215 (9)	0.0014 (8)	0.0003 (8)	0.0002 (8)
C12	0.0274 (11)	0.0338 (11)	0.0262 (10)	0.0061 (9)	0.0075 (8)	−0.0007 (9)
C13	0.0313 (11)	0.0270 (11)	0.0282 (10)	0.0059 (9)	0.0043 (9)	0.0020 (8)
C14	0.0248 (10)	0.0277 (10)	0.0229 (10)	0.0040 (8)	0.0000 (8)	−0.0013 (8)
C15	0.0280 (11)	0.0258 (11)	0.0250 (10)	0.0036 (8)	0.0019 (8)	0.0005 (8)
C16	0.0259 (10)	0.0335 (11)	0.0318 (11)	0.0004 (9)	0.0063 (9)	0.0048 (9)
C17	0.0271 (11)	0.0250 (10)	0.0344 (11)	0.0022 (9)	0.0054 (9)	0.0051 (8)
C18	0.0266 (11)	0.0368 (12)	0.0360 (11)	0.0048 (9)	0.0019 (9)	0.0020 (9)

O1—C16	1.398 (2)	C6—C7	1.394 (3)
O1—C17	1.436 (2)	C6—H6A	0.9500
O2—C18	1.418 (2)	C8—C9	1.396 (3)
O2—H2A	0.92 (3)	C8—C13	1.399 (3)
N1—C1	1.367 (2)	C9—C10	1.383 (3)
N1—C2	1.382 (2)	C9—H9A	0.9500
N1—H1A	0.89 (2)	C10—C11	1.393 (3)
N2—C1	1.325 (2)	C10—H10A	0.9500
N2—C7	1.394 (2)	C11—C12	1.398 (3)
N3—C15	1.346 (2)	C11—C14	1.471 (3)
N3—N4	1.349 (2)	C12—C13	1.382 (3)
N3—C16	1.458 (2)	C12—H12A	0.9500
N4—N5	1.318 (2)	C13—H13A	0.9500
N5—C14	1.371 (2)	C14—C15	1.374 (3)
C1—C8	1.465 (3)	C15—H15A	0.9500
C2—C3	1.390 (3)	C16—H16A	0.9900
C2—C7	1.404 (3)	C16—H16B	0.9900
C3—C4	1.383 (3)	C17—C18	1.506 (3)
C3—H3A	0.9500	C17—H17A	0.9900
C4—C5	1.402 (3)	C17—H17B	0.9900
C4—H4A	0.9500	C18—H18A	0.9900
C5—C6	1.381 (3)	C18—H18B	0.9900
C5—H5A	0.9500
C16—O1—C17	115.06 (14)	C8—C9—H9A	119.4
C18—O2—H2A	104.2 (16)	C9—C10—C11	120.37 (18)
C1—N1—C2	107.60 (16)	C9—C10—H10A	119.8
C1—N1—H1A	125.3 (13)	C11—C10—H10A	119.8
C2—N1—H1A	126.2 (14)	C10—C11—C12	118.60 (18)
C1—N2—C7	105.41 (15)	C10—C11—C14	120.69 (17)
C15—N3—N4	110.95 (15)	C12—C11—C14	120.70 (17)
C15—N3—C16	128.43 (16)	C13—C12—C11	121.04 (18)
N4—N3—C16	120.43 (15)	C13—C12—H12A	119.5
N5—N4—N3	107.03 (15)	C11—C12—H12A	119.5
N4—N5—C14	109.09 (15)	C12—C13—C8	120.37 (18)
N2—C1—N1	112.19 (17)	C12—C13—H13A	119.8
N2—C1—C8	125.05 (17)	C8—C13—H13A	119.8
N1—C1—C8	122.75 (17)	N5—C14—C15	107.68 (17)
N1—C2—C3	132.73 (18)	N5—C14—C11	122.44 (17)
N1—C2—C7	105.15 (16)	C15—C14—C11	129.88 (17)
C3—C2—C7	122.11 (18)	N3—C15—C14	105.25 (17)
C4—C3—C2	116.87 (19)	N3—C15—H15A	127.4
C4—C3—H3A	121.6	C14—C15—H15A	127.4
C2—C3—H3A	121.6	O1—C16—N3	112.07 (15)
C3—C4—C5	121.50 (19)	O1—C16—H16A	109.2
C3—C4—H4A	119.3	N3—C16—H16A	109.2
C5—C4—H4A	119.3	O1—C16—H16B	109.2
C6—C5—C4	121.51 (19)	N3—C16—H16B	109.2
C6—C5—H5A	119.2	H16A—C16—H16B	107.9
C4—C5—H5A	119.2	O1—C17—C18	106.53 (15)
C5—C6—C7	117.71 (19)	O1—C17—H17A	110.4
C5—C6—H6A	121.1	C18—C17—H17A	110.4
C7—C6—H6A	121.1	O1—C17—H17B	110.4
C6—C7—N2	130.04 (18)	C18—C17—H17B	110.4
C6—C7—C2	120.30 (18)	H17A—C17—H17B	108.6
N2—C7—C2	109.64 (16)	O2—C18—C17	111.68 (16)
C9—C8—C13	118.37 (17)	O2—C18—H18A	109.3
C9—C8—C1	121.16 (17)	C17—C18—H18A	109.3
C13—C8—C1	120.47 (17)	O2—C18—H18B	109.3
C10—C9—C8	121.20 (18)	C17—C18—H18B	109.3
C10—C9—H9A	119.4	H18A—C18—H18B	107.9
C15—N3—N4—N5	−0.3 (2)	C13—C8—C9—C10	−0.8 (3)
C16—N3—N4—N5	−175.62 (15)	C1—C8—C9—C10	178.93 (16)
N3—N4—N5—C14	0.3 (2)	C8—C9—C10—C11	−1.1 (3)
C7—N2—C1—N1	0.1 (2)	C9—C10—C11—C12	2.4 (3)
C7—N2—C1—C8	−178.63 (17)	C9—C10—C11—C14	−176.93 (17)
C2—N1—C1—N2	0.3 (2)	C10—C11—C12—C13	−1.9 (3)
C2—N1—C1—C8	179.09 (16)	C14—C11—C12—C13	177.50 (17)
C1—N1—C2—C3	−179.47 (19)	C11—C12—C13—C8	0.0 (3)
C1—N1—C2—C7	−0.60 (19)	C9—C8—C13—C12	1.4 (3)
N1—C2—C3—C4	178.25 (19)	C1—C8—C13—C12	−178.36 (17)
C7—C2—C3—C4	−0.5 (3)	N4—N5—C14—C15	−0.3 (2)
C2—C3—C4—C5	−0.2 (3)	N4—N5—C14—C11	−179.91 (16)
C3—C4—C5—C6	0.3 (3)	C10—C11—C14—N5	16.1 (3)
C4—C5—C6—C7	0.3 (3)	C12—C11—C14—N5	−163.22 (17)
C5—C6—C7—N2	−179.28 (18)	C10—C11—C14—C15	−163.43 (18)
C5—C6—C7—C2	−1.0 (3)	C12—C11—C14—C15	17.2 (3)
C1—N2—C7—C6	177.95 (19)	N4—N3—C15—C14	0.1 (2)
C1—N2—C7—C2	−0.5 (2)	C16—N3—C15—C14	174.99 (17)
N1—C2—C7—C6	−177.94 (16)	N5—C14—C15—N3	0.1 (2)
C3—C2—C7—C6	1.1 (3)	C11—C14—C15—N3	179.71 (18)
N1—C2—C7—N2	0.7 (2)	C17—O1—C16—N3	−77.18 (19)
C3—C2—C7—N2	179.71 (16)	C15—N3—C16—O1	−85.9 (2)
N2—C1—C8—C9	160.37 (18)	N4—N3—C16—O1	88.6 (2)
N1—C1—C8—C9	−18.3 (3)	C16—O1—C17—C18	−166.70 (15)
N2—C1—C8—C13	−19.9 (3)	O1—C17—C18—O2	169.44 (15)
N1—C1—C8—C13	161.50 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4i	0.89 (2)	2.50 (2)	3.244 (2)	141.7 (17)
N1—H1A···N5i	0.89 (2)	2.21 (2)	3.088 (2)	170.4 (19)
O2—H2A···N2ii	0.92 (3)	1.85 (3)	2.761 (2)	171 (2)
C15—H15A···O2iii	0.95	2.54	3.271 (2)	134
C16—H16A···O2iii	0.99	2.54	3.258 (2)	129
C17—H17B···O1iv	0.99	2.35	3.279 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N4i	0.89 (2)	2.50 (2)	3.244 (2)	141.7 (17)
N1—H1A⋯N5i	0.89 (2)	2.21 (2)	3.088 (2)	170.4 (19)
O2—H2A⋯N2ii	0.92 (3)	1.85 (3)	2.761 (2)	171 (2)
C15—H15A⋯O2iii	0.95	2.54	3.271 (2)	134
C16—H16A⋯O2iii	0.99	2.54	3.258 (2)	129
C17—H17B⋯O1iv	0.99	2.35	3.279 (2)	155

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