4-[3-(1H-Imidazol-1-yl)prop-yl]-3-methyl-5-(thio-phen-2-ylmeth-yl)-4H-1,2,4-triazole monohydrate.

In the title compound, C(14)H(17)N(5)S·H(2)O, the triazole ring makes dihedral angles of 48.15 (8) and 84.92 (8)° with the imidazole and thio-phenyl rings, respectively. The water mol-ecule is involved in inter-molecular O-H⋯N hydrogen bonding.

Related literature

For details of the synthesis, see: Ünver et al. (2009 ▶). For related structures, see: Fun et al. (2010 ▶); Kalkan et al. (2007 ▶); Ustabaş et al. (2007 ▶, 2009 ▶); Ünver et al. (2006 ▶). For the biological activity of triazoles, see: Ustabaş, et al. (2006a ▶,b ▶); Yılmaz et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H17N5S·H2O

M = 305.40

Monoclinic,

a = 9.5584 (12) Å

b = 9.4873 (10) Å

c = 17.644 (3) Å

β = 99.360 (12)°

V = 1578.7 (4) Å3

Z = 4

Cu Kα radiation

μ = 1.88 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.603, T max = 0.705

2855 measured reflections

2679 independent reflections

2336 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.137

S = 1.12

2679 reflections

200 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ZORTEP (Zsolnai, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004571X/jh2226sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004571X/jh2226Isup2.hkl

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

C14H17N5S·H2O	F(000) = 648
Mr = 305.40	Dx = 1.285 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
a = 9.5584 (12) Å	Cell parameters from 25 reflections
b = 9.4873 (10) Å	θ = 20–30°
c = 17.644 (3) Å	µ = 1.88 mm−1
β = 99.360 (12)°	T = 293 K
V = 1578.7 (4) Å3	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	2679 independent reflections
Radiation source: fine-focus sealed tube	2336 reflections with I > 2σ(I)
graphite	Rint = 0.016
Detector resolution: 2 pixels mm-1	θmax = 64.9°, θmin = 4.7°
ω–2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.603, Tmax = 0.705	l = −20→20
2855 measured reflections

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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0774P)2 + 0.5509P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
2679 reflections	Δρmax = 0.31 e Å−3
200 parameters	Δρmin = −0.34 e Å−3
3 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: 0.042 (2)

Experimental. North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 5 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

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
S1	0.37723 (6)	0.43126 (6)	0.61955 (4)	0.0582 (3)
N3	0.39660 (16)	0.21826 (17)	0.81129 (9)	0.0356 (4)
N1	0.61089 (18)	0.2561 (2)	0.78623 (10)	0.0442 (5)
N4	0.01247 (18)	−0.0268 (2)	0.74184 (11)	0.0456 (5)
N2	0.60666 (18)	0.29618 (19)	0.86153 (10)	0.0437 (5)
C4	0.3386 (2)	0.2567 (2)	0.62899 (11)	0.0410 (5)
C7	0.4785 (2)	0.2729 (2)	0.87518 (11)	0.0393 (5)
N5	−0.1397 (2)	0.0259 (3)	0.63795 (14)	0.0662 (6)
C9	0.2487 (2)	0.1719 (2)	0.80399 (12)	0.0410 (5)
H9A	0.2041	0.1797	0.7507	0.049*
H9B	0.1983	0.2336	0.8342	0.049*
C5	0.4407 (2)	0.1592 (2)	0.67757 (12)	0.0465 (5)
H5A	0.3968	0.0672	0.6789	0.056*
H5B	0.5246	0.1482	0.6537	0.056*
C3	0.2087 (2)	0.2246 (3)	0.58660 (12)	0.0494 (6)
H3	0.1678	0.1355	0.5844	0.059*
C12	0.0596 (2)	−0.0922 (3)	0.68159 (14)	0.0501 (6)
H12	0.1401	−0.1480	0.6836	0.060*
C8	0.4268 (3)	0.3028 (3)	0.94823 (13)	0.0592 (7)
H8A	0.5039	0.3365	0.9855	0.089*
H8B	0.3892	0.2180	0.9668	0.089*
H8C	0.3538	0.3731	0.9397	0.089*
C10	0.2361 (2)	0.0211 (2)	0.83060 (12)	0.0446 (5)
H10A	0.2792	0.0138	0.8842	0.053*
H10B	0.2880	−0.0403	0.8011	0.053*
C6	0.4841 (2)	0.2100 (2)	0.75747 (11)	0.0372 (5)
C2	0.1441 (2)	0.3447 (3)	0.54633 (14)	0.0570 (6)
H2	0.0564	0.3420	0.5145	0.068*
C1	0.2227 (3)	0.4610 (3)	0.55909 (15)	0.0586 (6)
H1	0.1960	0.5483	0.5374	0.070*
C13	−0.0351 (3)	−0.0591 (3)	0.61877 (15)	0.0588 (7)
H13	−0.0299	−0.0897	0.5692	0.071*
C11	0.0822 (2)	−0.0285 (3)	0.82172 (13)	0.0548 (6)
H11A	0.0798	−0.1236	0.8417	0.066*
H11B	0.0305	0.0320	0.8518	0.066*
C14	−0.1074 (2)	0.0419 (3)	0.71219 (17)	0.0590 (7)
H14	−0.1611	0.0948	0.7413	0.071*
O1W	0.8146 (3)	0.2886 (3)	1.00449 (18)	0.1142 (11)
H1W	0.758 (3)	0.312 (4)	0.9581 (11)	0.111 (13)*
H2W	0.801 (5)	0.341 (5)	1.0473 (14)	0.16 (2)*

	U11	U22	U33	U12	U13	U23
S1	0.0574 (4)	0.0422 (4)	0.0688 (5)	−0.0088 (2)	−0.0084 (3)	−0.0012 (3)
N3	0.0323 (8)	0.0379 (9)	0.0360 (8)	0.0000 (7)	0.0033 (6)	0.0008 (7)
N1	0.0393 (9)	0.0478 (11)	0.0460 (10)	−0.0052 (8)	0.0085 (7)	0.0062 (8)
N4	0.0333 (9)	0.0503 (11)	0.0529 (11)	−0.0075 (8)	0.0058 (7)	0.0015 (8)
N2	0.0399 (9)	0.0454 (10)	0.0439 (9)	−0.0064 (8)	0.0011 (7)	0.0028 (8)
C4	0.0495 (11)	0.0409 (11)	0.0327 (10)	−0.0069 (9)	0.0067 (8)	−0.0032 (8)
C7	0.0404 (10)	0.0398 (11)	0.0361 (10)	−0.0002 (8)	0.0017 (8)	0.0022 (8)
N5	0.0560 (13)	0.0636 (14)	0.0717 (14)	−0.0045 (11)	−0.0115 (11)	0.0065 (11)
C9	0.0293 (10)	0.0478 (12)	0.0450 (11)	0.0017 (8)	0.0031 (8)	0.0009 (9)
C5	0.0562 (13)	0.0422 (12)	0.0415 (11)	0.0023 (10)	0.0093 (10)	−0.0024 (9)
C3	0.0529 (13)	0.0553 (14)	0.0406 (11)	−0.0170 (10)	0.0090 (9)	−0.0014 (10)
C12	0.0404 (11)	0.0507 (13)	0.0604 (14)	−0.0112 (10)	0.0117 (10)	−0.0003 (11)
C8	0.0567 (14)	0.0789 (18)	0.0412 (12)	−0.0017 (13)	0.0053 (10)	−0.0093 (11)
C10	0.0368 (11)	0.0516 (13)	0.0440 (11)	−0.0037 (9)	0.0025 (8)	0.0046 (9)
C6	0.0394 (10)	0.0334 (10)	0.0393 (10)	0.0016 (8)	0.0081 (8)	0.0050 (8)
C2	0.0408 (12)	0.0800 (18)	0.0484 (13)	−0.0049 (11)	0.0021 (10)	−0.0044 (12)
C1	0.0578 (14)	0.0577 (15)	0.0579 (14)	0.0098 (12)	0.0017 (11)	0.0059 (11)
C13	0.0603 (15)	0.0606 (15)	0.0547 (14)	−0.0212 (12)	0.0066 (11)	−0.0003 (11)
C11	0.0428 (12)	0.0710 (16)	0.0514 (13)	−0.0128 (11)	0.0103 (10)	0.0055 (11)
C14	0.0404 (12)	0.0542 (15)	0.0798 (18)	−0.0017 (10)	0.0017 (11)	−0.0041 (12)
O1W	0.1007 (18)	0.106 (2)	0.113 (2)	0.0367 (15)	−0.0494 (16)	−0.0440 (17)

S1—C1	1.699 (3)	C5—H5B	0.9700
S1—C4	1.711 (2)	C3—C2	1.429 (4)
N3—C7	1.365 (3)	C3—H3	0.9300
N3—C6	1.366 (3)	C12—C13	1.349 (4)
N3—C9	1.466 (2)	C12—H12	0.9300
N1—C6	1.311 (3)	C8—H8A	0.9600
N1—N2	1.389 (3)	C8—H8B	0.9600
N4—C14	1.348 (3)	C8—H8C	0.9600
N4—C12	1.369 (3)	C10—C11	1.528 (3)
N4—C11	1.458 (3)	C10—H10A	0.9700
N2—C7	1.306 (3)	C10—H10B	0.9700
C4—C3	1.376 (3)	C2—C1	1.333 (4)
C4—C5	1.507 (3)	C2—H2	0.9300
C7—C8	1.481 (3)	C1—H1	0.9300
N5—C14	1.305 (4)	C13—H13	0.9300
N5—C13	1.369 (4)	C11—H11A	0.9700
C9—C10	1.516 (3)	C11—H11B	0.9700
C9—H9A	0.9700	C14—H14	0.9300
C9—H9B	0.9700	O1W—H1W	0.933 (10)
C5—C6	1.484 (3)	O1W—H2W	0.931 (10)
C5—H5A	0.9700
C1—S1—C4	92.43 (12)	C7—C8—H8A	109.5
C7—N3—C6	105.21 (16)	C7—C8—H8B	109.5
C7—N3—C9	126.96 (17)	H8A—C8—H8B	109.5
C6—N3—C9	127.76 (17)	C7—C8—H8C	109.5
C6—N1—N2	107.03 (16)	H8A—C8—H8C	109.5
C14—N4—C12	106.5 (2)	H8B—C8—H8C	109.5
C14—N4—C11	127.4 (2)	C9—C10—C11	112.50 (19)
C12—N4—C11	126.1 (2)	C9—C10—H10A	109.1
C7—N2—N1	107.71 (16)	C11—C10—H10A	109.1
C3—C4—C5	128.1 (2)	C9—C10—H10B	109.1
C3—C4—S1	110.58 (17)	C11—C10—H10B	109.1
C5—C4—S1	121.31 (16)	H10A—C10—H10B	107.8
N2—C7—N3	109.94 (18)	N1—C6—N3	110.11 (17)
N2—C7—C8	125.73 (19)	N1—C6—C5	125.08 (18)
N3—C7—C8	124.32 (19)	N3—C6—C5	124.80 (18)
C14—N5—C13	104.7 (2)	C1—C2—C3	112.9 (2)
N3—C9—C10	112.32 (16)	C1—C2—H2	123.5
N3—C9—H9A	109.1	C3—C2—H2	123.5
C10—C9—H9A	109.1	C2—C1—S1	112.2 (2)
N3—C9—H9B	109.1	C2—C1—H1	123.9
C10—C9—H9B	109.1	S1—C1—H1	123.9
H9A—C9—H9B	107.9	C12—C13—N5	110.7 (2)
C6—C5—C4	113.35 (18)	C12—C13—H13	124.7
C6—C5—H5A	108.9	N5—C13—H13	124.7
C4—C5—H5A	108.9	N4—C11—C10	112.13 (18)
C6—C5—H5B	108.9	N4—C11—H11A	109.2
C4—C5—H5B	108.9	C10—C11—H11A	109.2
H5A—C5—H5B	107.7	N4—C11—H11B	109.2
C4—C3—C2	111.9 (2)	C10—C11—H11B	109.2
C4—C3—H3	124.1	H11A—C11—H11B	107.9
C2—C3—H3	124.1	N5—C14—N4	112.3 (2)
C13—C12—N4	105.7 (2)	N5—C14—H14	123.8
C13—C12—H12	127.1	N4—C14—H14	123.8
N4—C12—H12	127.1	H1W—O1W—H2W	116.6 (17)
C6—N1—N2—C7	0.0 (2)	C4—C5—C6—N3	68.3 (3)
C1—S1—C4—C3	−0.50 (17)	C4—C3—C2—C1	−0.6 (3)
C1—S1—C4—C5	178.72 (18)	C3—C2—C1—S1	0.2 (3)
N1—N2—C7—N3	0.0 (2)	C4—S1—C1—C2	0.2 (2)
N1—N2—C7—C8	−179.0 (2)	N4—C12—C13—N5	0.3 (3)
C6—N3—C7—N2	−0.1 (2)	C14—N5—C13—C12	−0.5 (3)
C9—N3—C7—N2	177.05 (18)	C14—N4—C11—C10	−123.4 (3)
C6—N3—C7—C8	179.0 (2)	C12—N4—C11—C10	54.5 (3)
C9—N3—C7—C8	−3.9 (3)	C9—C10—C11—N4	61.6 (3)
C7—N3—C9—C10	−85.2 (2)	C13—N5—C14—N4	0.5 (3)
C6—N3—C9—C10	91.3 (2)	C12—N4—C14—N5	−0.3 (3)
C3—C4—C5—C6	−126.8 (2)	C11—N4—C14—N5	177.9 (2)
S1—C4—C5—C6	54.2 (2)	C3—C4—C5—C6	−126.8 (2)
C5—C4—C3—C2	−178.5 (2)	S1—C4—C5—C6	54.2 (2)
S1—C4—C3—C2	0.7 (2)	C4—C5—C6—N3	68.3 (3)
C14—N4—C12—C13	0.0 (2)	C4—C5—C6—N1	−110.2 (2)
C11—N4—C12—C13	−178.3 (2)	C5—C6—N3—C9	4.3 (3)
N3—C9—C10—C11	−178.95 (18)	C6—N3—C9—C10	91.3 (2)
N2—N1—C6—N3	0.0 (2)	N3—C9—C10—C11	−178.95 (18)
N2—N1—C6—C5	178.65 (19)	C9—C10—C11—N4	61.6 (3)
C7—N3—C6—N1	0.0 (2)	C10—C11—N4—C12	54.5 (3)
C9—N3—C6—N1	−177.03 (18)	C10—C11—N4—C14	−123.4 (3)
C7—N3—C6—C5	−178.63 (19)	C8—C7—N3—C9	−3.9 (3)
C9—N3—C6—C5	4.3 (3)	C7—N3—C9—C10	−85.2 (2)
C4—C5—C6—N1	−110.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···N5i	0.93 (1)	2.04 (2)	2.915 (4)	155 (4)
O1W—H1W···N2	0.93 (1)	2.05 (2)	2.948 (3)	161 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W⋯N5i	0.93 (1)	2.04 (2)	2.915 (4)	155 (4)
O1W—H1W⋯N2	0.93 (1)	2.05 (2)	2.948 (3)	161 (4)

Symmetry code: (i) .