4-[2-(4-Meth-oxy-phen-yl)eth-yl]-3-(thio-phen-2-ylmeth-yl)-1H-1,2,4-triazol-5(4H)-one monohydrate.

In the title compound, C(16)H(17)N(3)O(2)S·H(2)O, the triazole ring makes a dihedral angle of 34.63 (6)° with the benzene ring. The thio-phene ring is disordered over two orientations [occupancy ratio = 0.634 (4):0.366 (4)] which make dihedral angles of 54.61 (16) and 54.57 (31)° with the triazole ring. Inter-molecular N-H⋯O and O-H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For the biological activity of triazoles, see: Ünver et al. (2006 ▶); Ustabaş et al. (2007 ▶). For related structures, see: Ünver et al. (2006 ▶, 2010 ▶); Yılmaz et al. (2006 ▶). For the synthesis, see: Ünver et al. (2011 ▶).

Experimental

Crystal data

C16H17N3O2S·H2O

M = 333.40

Monoclinic,

a = 6.7945 (1) Å

b = 30.8791 (7) Å

c = 7.8564 (2) Å

β = 102.057 (1)°

V = 1611.97 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 292 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.901, T max = 0.962

30445 measured reflections

3176 independent reflections

2877 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 1.08

3176 reflections

240 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811045508/su2321sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045508/su2321Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045508/su2321Isup3.cml

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

C16H17N3O2S·H2O	F(000) = 704
Mr = 333.40	Dx = 1.374 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7004 reflections
a = 6.7945 (1) Å	θ = 2.6–32.1°
b = 30.8791 (7) Å	µ = 0.22 mm−1
c = 7.8564 (2) Å	T = 292 K
β = 102.057 (1)°	Block, colourless
V = 1611.97 (6) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII KappaCCD diffractometer	3176 independent reflections
Radiation source: fine-focus sealed tube	2877 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω and φ scan	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
Tmin = 0.901, Tmax = 0.962	k = −38→38
30445 measured reflections	l = −9→9

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0386P)2 + 0.4907P] where P = (Fo2 + 2Fc2)/3
3176 reflections	(Δ/σ)max < 0.001
240 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.23 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	Occ. (<1)
S1	0.5309 (3)	0.08013 (7)	0.3984 (2)	0.0486 (3)	0.634 (4)
C3	0.7012 (18)	0.1520 (3)	0.3706 (15)	0.083 (5)	0.634 (4)
H3	0.7865	0.1737	0.3470	0.099*	0.634 (4)
S1'	0.7024 (6)	0.15919 (17)	0.3771 (5)	0.0490 (6)	0.366 (4)
C3'	0.562 (2)	0.0828 (5)	0.386 (2)	0.083 (7)	0.366 (4)
H3'	0.5387	0.0531	0.3765	0.100*	0.366 (4)
O1	0.86927 (14)	0.01851 (4)	−0.29652 (13)	0.0451 (3)
O2	0.83597 (18)	0.25350 (4)	0.13401 (18)	0.0602 (3)
N1	0.61110 (16)	0.05605 (4)	0.01137 (15)	0.0377 (3)
N2	0.62048 (17)	0.03584 (4)	−0.14363 (15)	0.0381 (3)
H2A	0.510 (3)	0.0281 (6)	−0.213 (2)	0.052 (5)*
N3	0.92215 (15)	0.05475 (3)	−0.03060 (13)	0.0293 (2)
C1	0.4375 (3)	0.12019 (8)	0.4753 (2)	0.0672 (6)
H1	0.3274	0.1176	0.5278	0.081*
C2	0.5251 (3)	0.15777 (7)	0.4608 (2)	0.0710 (6)
H2	0.4850	0.1841	0.5001	0.085*
C4	0.7112 (2)	0.10794 (5)	0.32991 (17)	0.0362 (3)
C5	0.8700 (2)	0.08860 (5)	0.24723 (18)	0.0390 (3)
H5A	0.9634	0.1113	0.2317	0.047*
H5B	0.9446	0.0675	0.3267	0.047*
C6	0.79510 (18)	0.06713 (4)	0.07565 (16)	0.0311 (3)
C7	0.80746 (18)	0.03455 (4)	−0.17298 (16)	0.0319 (3)
C8	1.13309 (17)	0.06594 (4)	−0.02062 (17)	0.0328 (3)
H8A	1.2025	0.0414	−0.0577	0.039*
H8B	1.1963	0.0725	0.0991	0.039*
C9	1.1530 (2)	0.10497 (5)	−0.13524 (19)	0.0384 (3)
H9A	1.2942	0.1096	−0.1351	0.046*
H9B	1.0846	0.0987	−0.2539	0.046*
C10	1.0665 (2)	0.14568 (4)	−0.07543 (17)	0.0352 (3)
C11	1.1851 (2)	0.17298 (5)	0.0446 (2)	0.0442 (3)
H11	1.3213	0.1669	0.0821	0.053*
C12	1.1050 (2)	0.20875 (5)	0.1088 (2)	0.0493 (4)
H12	1.1876	0.2268	0.1878	0.059*
C13	0.9017 (2)	0.21811 (4)	0.0567 (2)	0.0422 (3)
C14	0.7812 (2)	0.19195 (5)	−0.0651 (2)	0.0430 (3)
H14	0.6453	0.1983	−0.1032	0.052*
C15	0.8653 (2)	0.15618 (5)	−0.12984 (18)	0.0397 (3)
H15	0.7839	0.1388	−0.2123	0.048*
C16	0.6266 (3)	0.26164 (7)	0.1030 (3)	0.0679 (5)
H16A	0.6017	0.2865	0.1685	0.102*
H16B	0.5590	0.2369	0.1382	0.102*
H16C	0.5769	0.2669	−0.0188	0.102*
O3	0.25229 (16)	0.02104 (4)	0.61748 (16)	0.0549 (3)
H3A	0.240 (3)	0.0083 (7)	0.520 (3)	0.065 (6)*
H3B	0.139 (3)	0.0193 (7)	0.649 (3)	0.072 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0394 (4)	0.0651 (8)	0.0458 (5)	−0.0037 (4)	0.0195 (4)	0.0000 (5)
C3	0.091 (6)	0.096 (10)	0.068 (5)	0.002 (4)	0.033 (4)	0.006 (4)
S1'	0.0614 (13)	0.0430 (8)	0.0430 (12)	−0.0015 (7)	0.0118 (9)	−0.0045 (7)
C3'	0.085 (10)	0.076 (9)	0.094 (9)	0.029 (7)	0.028 (5)	−0.040 (7)
O1	0.0340 (5)	0.0615 (7)	0.0416 (6)	−0.0025 (4)	0.0119 (4)	−0.0186 (5)
O2	0.0593 (7)	0.0431 (6)	0.0833 (9)	−0.0012 (5)	0.0266 (6)	−0.0127 (6)
N1	0.0279 (5)	0.0508 (7)	0.0362 (6)	−0.0035 (5)	0.0108 (5)	−0.0084 (5)
N2	0.0257 (5)	0.0530 (7)	0.0357 (6)	−0.0059 (5)	0.0066 (5)	−0.0119 (5)
N3	0.0225 (5)	0.0348 (5)	0.0313 (5)	−0.0004 (4)	0.0075 (4)	−0.0024 (4)
C1	0.0442 (9)	0.1205 (19)	0.0389 (9)	0.0111 (10)	0.0136 (7)	0.0021 (10)
C2	0.0837 (14)	0.0734 (13)	0.0498 (10)	0.0374 (11)	0.0000 (10)	−0.0188 (9)
C4	0.0367 (7)	0.0444 (8)	0.0279 (6)	−0.0004 (6)	0.0079 (5)	−0.0030 (6)
C5	0.0308 (6)	0.0527 (8)	0.0343 (7)	−0.0037 (6)	0.0087 (5)	−0.0071 (6)
C6	0.0260 (6)	0.0363 (7)	0.0324 (6)	0.0003 (5)	0.0093 (5)	−0.0006 (5)
C7	0.0274 (6)	0.0362 (7)	0.0328 (6)	−0.0010 (5)	0.0078 (5)	−0.0039 (5)
C8	0.0211 (6)	0.0394 (7)	0.0383 (7)	0.0006 (5)	0.0072 (5)	−0.0027 (5)
C9	0.0320 (6)	0.0437 (8)	0.0426 (7)	−0.0035 (6)	0.0149 (6)	−0.0003 (6)
C10	0.0348 (6)	0.0358 (7)	0.0363 (7)	−0.0040 (5)	0.0106 (5)	0.0049 (5)
C11	0.0315 (7)	0.0500 (8)	0.0504 (8)	−0.0054 (6)	0.0072 (6)	−0.0027 (7)
C12	0.0440 (8)	0.0482 (9)	0.0559 (9)	−0.0123 (7)	0.0105 (7)	−0.0120 (7)
C13	0.0481 (8)	0.0329 (7)	0.0496 (8)	−0.0030 (6)	0.0191 (7)	0.0030 (6)
C14	0.0354 (7)	0.0418 (8)	0.0500 (8)	0.0038 (6)	0.0047 (6)	0.0083 (6)
C15	0.0377 (7)	0.0396 (7)	0.0390 (7)	−0.0022 (6)	0.0013 (6)	0.0024 (6)
C16	0.0661 (11)	0.0635 (11)	0.0783 (13)	0.0186 (9)	0.0249 (10)	−0.0066 (10)
O3	0.0328 (5)	0.0859 (9)	0.0473 (6)	−0.0090 (5)	0.0111 (5)	−0.0282 (6)

S1—C1	1.568 (3)	C5—C6	1.4930 (18)
S1—C4	1.674 (2)	C5—H5A	0.9700
C3—C4	1.402 (10)	C5—H5B	0.9700
C3—C2	1.523 (13)	C8—C9	1.5273 (19)
C3—H3	0.9300	C8—H8A	0.9700
S1'—C2	1.488 (6)	C8—H8B	0.9700
S1'—C4	1.630 (5)	C9—C10	1.5037 (19)
C3'—C4	1.422 (14)	C9—H9A	0.9700
C3'—C1	1.666 (14)	C9—H9B	0.9700
C3'—H3'	0.9300	C10—C15	1.3833 (19)
O1—C7	1.2386 (15)	C10—C11	1.390 (2)
O2—C13	1.3695 (18)	C11—C12	1.373 (2)
O2—C16	1.415 (2)	C11—H11	0.9300
N1—C6	1.2928 (16)	C12—C13	1.387 (2)
N1—N2	1.3817 (16)	C12—H12	0.9300
N2—C7	1.3383 (16)	C13—C14	1.382 (2)
N2—H2A	0.867 (19)	C14—C15	1.388 (2)
N3—C7	1.3724 (16)	C14—H14	0.9300
N3—C6	1.3745 (16)	C15—H15	0.9300
N3—C8	1.4604 (15)	C16—H16A	0.9600
C1—C2	1.320 (3)	C16—H16B	0.9600
C1—H1	0.9300	C16—H16C	0.9600
C2—H2	0.9300	O3—H3A	0.85 (2)
C4—C5	1.4955 (18)	O3—H3B	0.86 (2)
C1—S1—C4	95.81 (15)	N1—C6—N3	111.59 (11)
C4—C3—C2	107.5 (8)	N1—C6—C5	126.14 (11)
C4—C3—H3	126.3	N3—C6—C5	122.20 (11)
C2—C3—H3	126.3	O1—C7—N2	129.52 (12)
C2—S1'—C4	98.2 (3)	O1—C7—N3	126.36 (11)
C4—C3'—C1	102.1 (9)	N2—C7—N3	104.12 (11)
C4—C3'—H3'	128.9	N3—C8—C9	111.22 (10)
C1—C3'—H3'	128.9	N3—C8—H8A	109.4
C13—O2—C16	118.32 (14)	C9—C8—H8A	109.4
C6—N1—N2	104.18 (10)	N3—C8—H8B	109.4
C7—N2—N1	112.67 (11)	C9—C8—H8B	109.4
C7—N2—H2A	127.8 (11)	H8A—C8—H8B	108.0
N1—N2—H2A	119.2 (11)	C10—C9—C8	112.76 (11)
C7—N3—C6	107.44 (10)	C10—C9—H9A	109.0
C7—N3—C8	122.35 (10)	C8—C9—H9A	109.0
C6—N3—C8	129.45 (11)	C10—C9—H9B	109.0
C2—C1—S1	115.75 (16)	C8—C9—H9B	109.0
C2—C1—C3'	107.2 (5)	H9A—C9—H9B	107.8
S1—C1—C3'	8.5 (5)	C15—C10—C11	117.57 (13)
C2—C1—H1	122.1	C15—C10—C9	121.67 (12)
S1—C1—H1	122.1	C11—C10—C9	120.67 (12)
C3'—C1—H1	130.6	C12—C11—C10	121.30 (13)
C1—C2—S1'	119.0 (2)	C12—C11—H11	119.4
C1—C2—C3	110.4 (4)	C10—C11—H11	119.4
S1'—C2—C3	8.6 (6)	C11—C12—C13	120.37 (14)
C1—C2—H2	124.8	C11—C12—H12	119.8
S1'—C2—H2	116.2	C13—C12—H12	119.8
C3—C2—H2	124.8	O2—C13—C14	124.94 (14)
C3—C4—C3'	112.7 (8)	O2—C13—C12	115.59 (14)
C3—C4—C5	124.1 (6)	C14—C13—C12	119.47 (14)
C3'—C4—C5	123.1 (6)	C13—C14—C15	119.30 (13)
C3—C4—S1'	0.7 (7)	C13—C14—H14	120.3
C3'—C4—S1'	113.3 (6)	C15—C14—H14	120.3
C5—C4—S1'	123.4 (2)	C10—C15—C14	121.95 (13)
C3—C4—S1	110.5 (6)	C10—C15—H15	119.0
C3'—C4—S1	2.2 (7)	C14—C15—H15	119.0
C5—C4—S1	125.30 (14)	O2—C16—H16A	109.5
S1'—C4—S1	111.2 (2)	O2—C16—H16B	109.5
C6—C5—C4	115.37 (11)	H16A—C16—H16B	109.5
C6—C5—H5A	108.4	O2—C16—H16C	109.5
C4—C5—H5A	108.4	H16A—C16—H16C	109.5
C6—C5—H5B	108.4	H16B—C16—H16C	109.5
C4—C5—H5B	108.4	H3A—O3—H3B	107.9 (19)
H5A—C5—H5B	107.5
C6—N1—N2—C7	0.15 (16)	S1—C4—C5—C6	64.33 (18)
C4—S1—C1—C2	−0.15 (19)	N2—N1—C6—N3	−0.32 (15)
C4—S1—C1—C3'	−2(4)	N2—N1—C6—C5	−177.25 (13)
C4—C3'—C1—C2	−0.6 (9)	C7—N3—C6—N1	0.38 (15)
C4—C3'—C1—S1	178 (5)	C8—N3—C6—N1	170.39 (12)
S1—C1—C2—S1'	−0.8 (3)	C7—N3—C6—C5	177.45 (12)
C3'—C1—C2—S1'	−0.5 (6)	C8—N3—C6—C5	−12.5 (2)
S1—C1—C2—C3	−0.3 (5)	C4—C5—C6—N1	−15.2 (2)
C3'—C1—C2—C3	−0.1 (7)	C4—C5—C6—N3	168.18 (12)
C4—S1'—C2—C1	1.2 (3)	N1—N2—C7—O1	178.89 (14)
C4—S1'—C2—C3	−1(4)	N1—N2—C7—N3	0.07 (15)
C4—C3—C2—C1	0.7 (8)	C6—N3—C7—O1	−179.12 (13)
C4—C3—C2—S1'	178 (4)	C8—N3—C7—O1	10.0 (2)
C2—C3—C4—C3'	−1.2 (10)	C6—N3—C7—N2	−0.25 (14)
C2—C3—C4—C5	−177.1 (3)	C8—N3—C7—N2	−171.14 (11)
C2—C3—C4—S1'	−157.00 (5)	C7—N3—C8—C9	74.50 (15)
C2—C3—C4—S1	−0.8 (7)	C6—N3—C8—C9	−94.21 (15)
C1—C3'—C4—C3	1.1 (11)	N3—C8—C9—C10	64.61 (14)
C1—C3'—C4—C5	177.1 (3)	C8—C9—C10—C15	−87.12 (16)
C1—C3'—C4—S1'	1.4 (10)	C8—C9—C10—C11	89.39 (15)
C1—C3'—C4—S1	−8(17)	C15—C10—C11—C12	0.9 (2)
C2—S1'—C4—C3	23.00 (3)	C9—C10—C11—C12	−175.74 (14)
C2—S1'—C4—C3'	−1.6 (7)	C10—C11—C12—C13	0.9 (2)
C2—S1'—C4—C5	−177.30 (15)	C16—O2—C13—C14	7.3 (2)
C2—S1'—C4—S1	−1.2 (2)	C16—O2—C13—C12	−172.27 (16)
C1—S1—C4—C3	0.6 (5)	C11—C12—C13—O2	177.43 (14)
C1—S1—C4—C3'	172 (18)	C11—C12—C13—C14	−2.2 (2)
C1—S1—C4—C5	176.87 (13)	O2—C13—C14—C15	−178.05 (14)
C1—S1—C4—S1'	0.9 (2)	C12—C13—C14—C15	1.5 (2)
C3—C4—C5—C6	−119.9 (6)	C11—C10—C15—C14	−1.6 (2)
C3'—C4—C5—C6	64.6 (8)	C9—C10—C15—C14	175.04 (13)
S1'—C4—C5—C6	−120.2 (2)	C13—C14—C15—C10	0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.867 (19)	1.975 (19)	2.8334 (16)	170.3 (16)
O3—H3A···O1ii	0.85 (2)	1.95 (2)	2.7679 (15)	163.6 (19)
O3—H3B···O1iii	0.86 (2)	1.97 (2)	2.8231 (15)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.867 (19)	1.975 (19)	2.8334 (16)	170.3 (16)
O3—H3A⋯O1ii	0.85 (2)	1.95 (2)	2.7679 (15)	163.6 (19)
O3—H3B⋯O1iii	0.86 (2)	1.97 (2)	2.8231 (15)	175 (2)

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