4-[3-(1H-Imidazol-1-yl)prop­yl]-3-methyl-5-(thio­phen-2-ylmeth­yl)-4H-1,2,4-triazole monohydrate

Gurumoorthy, A.; Gopalsamy, V.; Ünlüer, D.; Kör, G.; Ramamurthi, K.

doi:10.1107/S160053681004571X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages o3150-o3151

https://doi.org/10.1107/S160053681004571X

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4-[3-(1H-Imidazol-1-yl)propyl]-3-methyl-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole monohydrate

Anuradha Gurumoorthy,^a Vasuki Gopalsamy,^b ^* Dilek Ünlüer,^c Gülcan Kör ^c and K. Ramamurthi ^d

^aDepartment of Physics, Saveetha School of Engineering, Saveetha University, Chennai-5, India, ^bDepartment of Physics, Kunthavai Naachiar Government Arts College (w) (Autonomous), Thanjavur-7, India, ^cDepartment of Chemistry, Faculty of Arts and Sciences, Karadeniz Teknik University, Trabzon 61080, Turkey, and ^dCrystal Growth and Thin Film Laboratory, School of Physics, Bharathidasan University, Tiruchirappalli-24, India
^*Correspondence e-mail: vasuki.arasi@yahoo.com

(Received 21 October 2010; accepted 7 November 2010; online 13 November 2010)

In the title compound, C₁₄H₁₇N₅S·H₂O, the triazole ring makes dihedral angles of 48.15 (8) and 84.92 (8)° with the imidazole and thiophenyl rings, respectively. The water molecule is involved in intermolecular 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_r = 305.40
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.137
S = 1.12
2679 reflections
200 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004571X/jh2226Isup2.hkl

checkCIF report

Comment top

Triazole compounds and their derivatives have many applications in industry and medicine. Ionic liquids consisting of imidazolium and triazolium salts have attracted increasing interest as an alternative to classical organic solvents for a wide range of chemical syntheses, biocatalysis, electrochemical applications, energetic materials, nano-rods, liquid-liquid separation and polymerization. These interesting liquids containing imidazole and triazole ring systems have unique physical and chemical properties: low melting point, very low vapour pressure, a large liquid phase range, tunable miscibility, and good hydrolytic and thermal stability (Ustabaş et al., 2006). In the field of medicine triazole derivatives were reported to exhibit various pharmacological activities such as antimicrobial, analgesic, anti- inflammatory, anticancer and antioxidant properties. A few derivatives of triazoles have exhibited antimicrobial activity. Some of the drugs such as ribavirin (antiviral agent), rizatriptan (anti migraine agent), alprazolam (anxiolytic agent), fluconazole and itraconazole (antifungal agents) are the best examples for potent molecules possessing the triazole nucleus (Fun et al., 2010). Furthermore, in many compounds, the thiophene unit is associated with high anticancer and antifungal activity (Kalkan et al., 2007). In a previous paper, we reported the 1,2,4 triazole derivative with different substituents. We report here the crystal structure of the title compound (I) (Fig.1) in order to examine the structure activity of 1,2,4 triazole with a thiophene substituent.

Compound (I) contains three planar rings (Fig.1), namely a triazole ring N1/N2/C7/N3/C6 (A), an imidazole ring N4/C12/C13/N5/C14 (B) and a thiophene ring C1/C2/C3/C4/S1 (C). The dihedral angle between rings A/B, A/C and B/C are 48.15 (8)°, 84.92 (8)° and 74.73 (9)°, respectively. In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The C—N bond lengths in the triazole ring of all molecules lie in the range of 1.260 (3)–1.349 (4) Å. These are longer than a typical double C═N bond [1.269 (2) Å], but shorter than a C—N single bond [1.443 (4) Å]. The bond length N2—C7 [1.306 (3) Å] and N3—C7 [1.365 (3) Å] are in agreement with the corresponding values in similar structures containing triazole ring such as [1.290 (3)Å and 1.384 (3) Å; Yılmaz et al., 2006], [1.287 (4)Å and 1.374 (4) Å; Ustabaş et al., 2007] and [1.292 (3)Å and 1.373 (3) Å; Ustabaş et al., 2009]. The N1—N2 [1.389 (3) Å] bond length is close to that reported for similar compounds [1.388 (2)Å Ünver et al., 2006] and [1.398 (4)Å Ustabaş, Çoruh, Sancak, Ünver & Vázquez-López (2006)]. Atom N3 has a trigonal configuration, the sum of three bond angles around them being 360° (Kalkan et al., 2007). The bond lengths and angles in the imidazole and thiophenyl rings are normal. In the thiophenyl ring S1—C4 [1.711 (2) Å] bond is longer than S1—C1 [1.699 (3) Å] bond. These S—C distances are in agreement with the corresponding values of those found in other structures containing thiophene, [1.706 (2)Å and 1.723 (2) Å; Ünver et al., 2006], [1.710 (5)Å and 1.724 (4) Å; Ustabaş,Çoruh, Sancak, Ünver & Vázquez-López (2006)],[1.701 (3)Å and 1.712 (2) Å; Yılmaz et al., 2006], [1.685 (5)Å and 1.692 (6) Å; Ustabaş et al., 2007] and [1.698 (3)Å and 1.735 (6) Å; Ustabaş et al., 2009]. The exocyclic bond angles N1—C6—C5 and N2—C7—C8 are 125.08 (18)° and 125.73 (19)°, respectively. These increase from the normal value of 120° might be the consequence of repulsion between the lone pair of electrons on atom N1 and H5B attached to C5(N1···H5B = 2.563 Å) and on atom N2 and H8A attached to C8(N2···H8B = 2.566 Å), respectively. The widening of the excocyclic angles N3—C9—C10 [112.3 (16)°]and C9—C10—C11 [112.5 (19)°] from the normal 109° may be due to the steric repulsion between H8B and H10A (H8B ··· H10A = 2.547 Å) and H9A and H10B (H9A··· H10B = 2.357 Å), respectively. The C10—C11—N4 exocyclic angle [112.13 (18)°] deviate from the normal value of 109° may be due to the consequence of repulsion between the lone pair of electrons on atom N4 and H11A and H11B attached to C11 (N4···H11A = 1.998Å and N4···H11B = 1.998 Å). The C11—N4—C14 exocyclic angle [127.4 (2)°] significantly deviate from the normal value of 120° may be due to the consequence of repulsion between the lone pair of electrons on atom N4 and H14 at C14 (N4···H14 = 2.019 Å). The N3—C9—C10—C11 torsion angle of 178.95 (18)° indicates that the triazole ring and the immidazole moiety has an E-Configuration across the C9—C10 bond. The C9—N3—C6—C5 torsion angle of 4.3 (3)° indicates that the imidazole moiety and the thiophenyl moiety are in Z-Configuration across the N3—N6 bond. The water molecule is involved in the intermolecular O–H···N hydrogen bonding (Table 2), which is effective in stabilizing the crystal structure.

Related literature top

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 top

The compound was synthesized by published method (Ünver et al.,2009)

Structure description top

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing of the title compound viewed along the c axis. Intermolecular O—H···N hydrogen bonds are shown as dashed lines.
	Fig. 3. Crystal Packing of the title compound with hydrogen bonds.
	Fig. 4. Crystal packing of the title compound viewed along the c axis. Intermolecular O—H···N hydrogen bonds are shown as dashed lines.

4-[3-(1H-Imidazol-1-yl)propyl]-3-methyl-5-(thiophen-2-ylmethyl)- 4H-1,2,4-triazole monohydrate top

Crystal data top

C₁₄H₁₇N₅S·H₂O	F(000) = 648
M_r = 305.40	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0774P)² + 0.5509P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
2679 reflections	Δρ_max = 0.31 e Å⁻³
200 parameters	Δρ_min = −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)

Crystal data top

C₁₄H₁₇N₅S·H₂O	V = 1578.7 (4) Å³
M_r = 305.40	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 9.5584 (12) Å	µ = 1.88 mm⁻¹
b = 9.4873 (10) Å	T = 293 K
c = 17.644 (3) Å	0.30 × 0.25 × 0.20 mm
β = 99.360 (12)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2679 independent reflections
Absorption correction: ψ scan (North et al., 1968)	2336 reflections with I > 2σ(I)
T_min = 0.603, T_max = 0.705	R_int = 0.016
2855 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	3 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.31 e Å⁻³
2679 reflections	Δρ_min = −0.34 e Å⁻³
200 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₇N₅S·H₂O
M_r	305.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.5584 (12), 9.4873 (10), 17.644 (3)
β (°)	99.360 (12)
V (Å³)	1578.7 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.88
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.603, 0.705
No. of measured, independent and observed [I > 2σ(I)] reflections	2855, 2679, 2336
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.587

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.137, 1.12
No. of reflections	2679
No. of parameters	200
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.34

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), MolEN (Fair, 1990), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and ZORTEP (Zsolnai, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···N5ⁱ	0.931 (10)	2.04 (2)	2.915 (4)	155 (4)
O1W—H1W···N2	0.933 (10)	2.051 (17)	2.948 (3)	161 (4)

Symmetry code: (i) x+1, −y+1/2, z+1/2.

Acknowledgements

VG thanks the UGC, India, for financial assistance under a Minor Research Project (2010–2011) and also thanks the Regional Sophisticated Instrumentation Centre for the data collection. DÜ and GK thank the Research Fund of Karadeniz Technical University for its support of this work.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orphen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
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Fun, H.-K., Quah, C. K., Vijesh, A. M., Malladi, S. & Isloor, A. M. (2010). Acta Cryst. E66, o29–o30. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 66| Part 12| December 2010| Pages o3150-o3151

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

4-[3-(1H-Imidazol-1-yl)prop­yl]-3-methyl-5-(thio­phen-2-ylmeth­yl)-4H-1,2,4-triazole monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-[3-(1H-Imidazol-1-yl)propyl]-3-methyl-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole monohydrate