3-(Adamantan-1-yl)-4-ethyl-1-{[4-(2-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-1H-1,2,4-triazole-5(4H)-thione

El-Emam, A.A.; Al-Tuwaijri, H.M.; Al-Abdullah, E.S.; Chidan Kumar, C.S.; Fun, H.-K.

doi:10.1107/S1600536813032789

organic compounds

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ISSN: 2056-9890

Volume 70| Part 1| January 2014| Pages o25-o26

https://doi.org/10.1107/S1600536813032789

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3-(Adamantan-1-yl)-4-ethyl-1-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-1H-1,2,4-triazole-5(4H)-thione

Ali A. El-Emam,^a ‡ Hanaa M. Al-Tuwaijri,^a Ebtehal S. Al-Abdullah,^a C. S. Chidan Kumar ^b and Hoong-Kun Fun ^a ^*§

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riaydh 11451, Saudi Arabia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hfun.c@ksu.edu.sa

(Received 28 November 2013; accepted 3 December 2013; online 7 December 2013)

In the title compound, C₂₆H₃₇N₅OS, the piperazine ring adopts a chair conformation. The triazole ring forms dihedral angles of 67.85 (9) and 59.41 (9)° with the piperazine and benzene rings, respectively, resulting in an approximate V-shaped conformation for the molecule. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure features C—H⋯π interactions, producing a two-dimensional supramolecular architecture.

CCDC reference: 974874

Related literature

For the pharmacological activity of adamantane derivatives and adamantyl-1,2,4-triazoles, see: Togo et al. (1968 ); El-Emam et al. (2004 , 2013 ); Al-Deeb et al. (2006 ); Kadi et al. (2007 , 2010 ). For related adamantyl-1,2,4-triazole structures, see: Al-Abdullah et al. (2013 ); Al-Tamimi, Alafeefy et al. (2013 ); Al-Tamimi, Al-Abdullah et al. (2013 ); El-Emam et al. (2012 ). For the synthesis of the starting material, see: El-Emam & Ibrahim (1991 ). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₆H₃₇N₅OS
M_r = 467.67
Monoclinic, C 2/c
a = 19.8170 (3) Å
b = 11.9384 (3) Å
c = 21.7807 (4) Å
β = 107.886 (2)°
V = 4903.90 (17) Å³
Z = 8
Cu Kα radiation
μ = 1.39 mm⁻¹
T = 296 K
0.98 × 0.62 × 0.41 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.344, T_max = 0.599
15455 measured reflections
4029 independent reflections
3606 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.115
S = 1.05
4029 reflections
308 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1	0.97	2.26	2.903 (2)	123
C18—H18A⋯Cgⁱ	0.97	2.81	3.748 (2)	162
Symmetry code: (i) $[x-1, -y-1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 974874

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813032789/rz5099sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032789/rz5099Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813032789/rz5099Isup3.cml

checkCIF report

Comment top

Derivatives of adamantane have long been known for their diverse biological activities including antiviral activity against influenza (Togo et al., 1968) and HIV viruses (El-Emam et al., 2004). Moreover, adamantane derivative were reported to exhibit marked antibacterial and anti-inflammatory activities (Kadi et al., 2007, 2010; El-Emam et al., 2013). In continuation of our interest in the chemical and pharmacological properties of adamantane derivatives, and as part of our on-going structural studies of adamantane derivatives (Al-Abdullah et al., 2013); Al-Tamimi, Alafeefy et al., 2013; Al-Tamimi, Al-Abdullah et al., 2013; El-Emam et al., 2012), we have synthesized the title compound (I) as a potential chemotherapeutic agent.

In the crystal structure of the title compound (Fig. 1), the piperazine (N1–N2/C8–C11) ring adopts a chair conformation with puckering parameters: Q = 0.5783 (18) Å, θ = 178.03 (17)°, and φ = 25 (5)° (Cremer & Pople, 1975). The dihedral angle between the piperazine ring and the triazole ring (N3–N5/C13/C14) is 67.85 (9)°. The triazole ring forms a dihedral angle of 59.41 (9)° with the benzene ring (C1—C6), resulting in an approximate V-shape conformation of the molecule. An intramolecular C–H···O hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). The crystal structure features an intermolecular C–H···π interaction with a H18A···Cg distance of 2.81 Å, where Cg is the centroid of the benzene ring (C1—C6).

Related literature top

For the pharmacological activity of adamantane derivatives and adamantyl-1,2,4-triazoles, see: Togo et al. (1968); El-Emam et al. (2004, 2013); Al-Deeb et al. (2006); Kadi et al. (2007, 2010). For related adamantyl-1,2,4-triazole structures, see: Al-Abdullah et al. (2013); Al-Tamimi, Alafeefy et al. (2013); Al-Tamimi, Al-Abdullah et al. (2013); El-Emam et al. (2012). For the synthesis of the starting material, see: El-Emam & Ibrahim (1991). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 527 mg (2 mmol) of 3-(1-adamantyl)-4-ethyl-4H-1,2,4- triazole-5-thiol (El-Emam & Ibrahim, 1991), 1-(2-methoxyphenyl)piperazine (383 mg, 2 mmol) and 37% formaldehyde solution (1 ml) in ethanol (8 ml) was heated under reflux for 15 min until a clear solution was obtained. Stirring was continued for 12 h at room temperature and the mixture was allowed to stand overnight. Cold water (5 ml) was added slowly and the mixture was stirred for 20 min. The precipitated crude product were filtered, washed with water, dried, and crystallized from ethanol to yield 860 mg (92%) of the title compound (C₂₆H₃₇N₅OS) as colourless needle crystals. M.p.: 477–479 K. Single plate-shaped crystals suitable for X-ray analysis were obtained by slow evaporation of a CHCl₃:EtOH solution (1:1 v/v; 5 ml) at room temperature.

¹H NMR (CDCl₃, 500.13 MHz): δ 1.32 (t, 3H, CH₂CH₃, J = 7.0 Hz), 1.71–1.76 (m, 6H, Adamantane-H), 1.98–2.12 (m, 9H, Adamantane-H), 3.08 (s, 8H, Piperazine-H), 3.81 (s, 3H, OCH₃), 4.15 (q, 2H, CH₂CH₃, J = 7.0 Hz), 5.15 (s, 2H, CH₂), 6.79–7.01 (m, 4H, Ar—H). ¹³C NMR (CDCl₃, 125.76 MHz): δ 13.76 (CH₂CH₃), 27.92, 35.32, 36.48, 39.83 (Adamantane-C), 43.83 (CH₂CH₃), 47.40, 50.18 (Piperazine-C), 55.48 (OCH₃), 72.58 (CH₂), 111.43, 118.38, 121.12, 123.55, 152.13, 152.26 (Ar—C), 156.57 (Triazole C-5), 167.34 (C=S).

Structure description top

For the pharmacological activity of adamantane derivatives and adamantyl-1,2,4-triazoles, see: Togo et al. (1968); El-Emam et al. (2004, 2013); Al-Deeb et al. (2006); Kadi et al. (2007, 2010). For related adamantyl-1,2,4-triazole structures, see: Al-Abdullah et al. (2013); Al-Tamimi, Alafeefy et al. (2013); Al-Tamimi, Al-Abdullah et al. (2013); El-Emam et al. (2012). For the synthesis of the starting material, see: El-Emam & Ibrahim (1991). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids. The intramolecular hydrogen bond is shown as a dashed line.

3-(Adamantan-1-yl)-4-ethyl-1-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₂₆H₃₇N₅OS	F(000) = 2016
M_r = 467.67	D_x = 1.267 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 4154 reflections
a = 19.8170 (3) Å	θ = 4.3–69.2°
b = 11.9384 (3) Å	µ = 1.39 mm⁻¹
c = 21.7807 (4) Å	T = 296 K
β = 107.886 (2)°	Plate, colourless
V = 4903.90 (17) Å³	0.98 × 0.62 × 0.41 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	4029 independent reflections
Radiation source: fine-focus sealed tube	3606 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 65.0°, θ_min = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→23
T_min = 0.344, T_max = 0.599	k = −9→14
15455 measured reflections	l = −25→21

Refinement top

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0627P)² + 2.6908P] where P = (F_o² + 2F_c²)/3
4029 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₆H₃₇N₅OS	V = 4903.90 (17) Å³
M_r = 467.67	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 19.8170 (3) Å	µ = 1.39 mm⁻¹
b = 11.9384 (3) Å	T = 296 K
c = 21.7807 (4) Å	0.98 × 0.62 × 0.41 mm
β = 107.886 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4029 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3606 reflections with I > 2σ(I)
T_min = 0.344, T_max = 0.599	R_int = 0.033
15455 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.19 e Å⁻³
4029 reflections	Δρ_min = −0.27 e Å⁻³
308 parameters

Special details top

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	0.04659 (3)	0.66541 (4)	0.36270 (3)	0.06079 (18)
O1	−0.25953 (6)	1.15940 (11)	0.28999 (6)	0.0511 (3)
N1	−0.12211 (7)	1.09436 (12)	0.31028 (6)	0.0392 (3)
N2	−0.03369 (7)	0.95212 (11)	0.40765 (7)	0.0401 (3)
N3	−0.04059 (7)	0.74873 (11)	0.42680 (7)	0.0410 (3)
N4	−0.09869 (7)	0.71981 (11)	0.44558 (7)	0.0402 (3)
N5	−0.06803 (7)	0.58126 (11)	0.39235 (6)	0.0380 (3)
C1	−0.21966 (9)	1.22602 (15)	0.26341 (8)	0.0414 (4)
C2	−0.24588 (10)	1.32048 (17)	0.22721 (9)	0.0531 (5)
H2A	−0.2916	1.3448	0.2233	0.064*
C3	−0.20535 (12)	1.37922 (18)	0.19688 (10)	0.0612 (5)
H3A	−0.2239	1.4422	0.1723	0.073*
C4	−0.13806 (12)	1.34470 (18)	0.20304 (10)	0.0609 (5)
H4A	−0.1110	1.3826	0.1816	0.073*
C5	−0.11006 (10)	1.25299 (16)	0.24133 (9)	0.0502 (4)
H5A	−0.0636	1.2317	0.2460	0.060*
C6	−0.14894 (9)	1.19165 (14)	0.27302 (8)	0.0392 (4)
C7	−0.33410 (10)	1.17746 (19)	0.27037 (11)	0.0604 (5)
H7A	−0.3564	1.1195	0.2879	0.091*
H7B	−0.3523	1.1760	0.2241	0.091*
H7C	−0.3439	1.2490	0.2859	0.091*
C8	−0.05394 (9)	1.05442 (15)	0.30672 (9)	0.0442 (4)
H8A	−0.0175	1.1089	0.3266	0.053*
H8B	−0.0560	1.0466	0.2619	0.053*
C9	−0.03495 (9)	0.94278 (15)	0.34052 (9)	0.0447 (4)
H9A	−0.0695	0.8868	0.3187	0.054*
H9B	0.0112	0.9190	0.3388	0.054*
C10	−0.10279 (9)	0.98856 (14)	0.41065 (8)	0.0407 (4)
H10A	−0.1018	0.9943	0.4553	0.049*
H10B	−0.1385	0.9339	0.3894	0.049*
C11	−0.12140 (9)	1.10112 (15)	0.37793 (8)	0.0420 (4)
H11A	−0.1677	1.1245	0.3796	0.050*
H11B	−0.0869	1.1565	0.4006	0.050*
C12	−0.00463 (9)	0.85666 (15)	0.44685 (9)	0.0449 (4)
C13	−0.02030 (9)	0.66608 (14)	0.39407 (8)	0.0419 (4)
C14	−0.11453 (8)	0.61806 (13)	0.42412 (8)	0.0361 (4)
C15	−0.06398 (9)	0.47423 (15)	0.36034 (9)	0.0460 (4)
H15A	−0.0532	0.4888	0.3205	0.055*
H15B	−0.1098	0.4374	0.3494	0.055*
C16	−0.00816 (11)	0.39690 (17)	0.40219 (12)	0.0619 (5)
H16A	−0.0079	0.3279	0.3796	0.093*
H16B	−0.0187	0.3818	0.4416	0.093*
H16C	0.0375	0.4319	0.4120	0.093*
C17	−0.17657 (8)	0.55496 (13)	0.43342 (8)	0.0364 (4)
C18	−0.23590 (9)	0.54186 (17)	0.36848 (9)	0.0499 (5)
H18A	−0.2510	0.6151	0.3501	0.060*
H18B	−0.2181	0.5003	0.3384	0.060*
C19	−0.29894 (10)	0.4796 (2)	0.37923 (10)	0.0603 (5)
H19A	−0.3360	0.4702	0.3378	0.072*
C20	−0.27523 (11)	0.36486 (17)	0.40858 (10)	0.0565 (5)
H20A	−0.3155	0.3246	0.4142	0.068*
H20B	−0.2563	0.3216	0.3799	0.068*
C21	−0.21867 (10)	0.37929 (14)	0.47347 (9)	0.0475 (4)
H21A	−0.2040	0.3053	0.4924	0.057*
C22	−0.15471 (9)	0.43877 (14)	0.46354 (8)	0.0410 (4)
H22A	−0.1357	0.3944	0.4354	0.049*
H22B	−0.1180	0.4469	0.5047	0.049*
C23	−0.20662 (11)	0.62237 (15)	0.47925 (10)	0.0507 (5)
H23A	−0.2210	0.6960	0.4612	0.061*
H23B	−0.1702	0.6319	0.5204	0.061*
C24	−0.27071 (11)	0.56134 (16)	0.48944 (11)	0.0560 (5)
H24A	−0.2893	0.6053	0.5186	0.067*
C25	−0.24790 (12)	0.44675 (16)	0.51877 (10)	0.0559 (5)
H25A	−0.2118	0.4550	0.5603	0.067*
H25B	−0.2881	0.4081	0.5254	0.067*
C26	−0.32823 (11)	0.54824 (19)	0.42461 (13)	0.0687 (6)
H26A	−0.3431	0.6214	0.4060	0.082*
H26B	−0.3691	0.5107	0.4307	0.082*
H12B	0.0444 (11)	0.8413 (14)	0.4491 (9)	0.041 (5)*
H12A	−0.0064 (10)	0.8708 (16)	0.4920 (10)	0.047 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0474 (3)	0.0637 (3)	0.0818 (4)	−0.0027 (2)	0.0354 (3)	0.0117 (3)
O1	0.0367 (6)	0.0607 (8)	0.0589 (7)	0.0015 (5)	0.0190 (6)	0.0018 (6)
N1	0.0369 (7)	0.0470 (8)	0.0371 (7)	0.0033 (6)	0.0162 (6)	0.0050 (6)
N2	0.0353 (7)	0.0400 (7)	0.0438 (7)	−0.0084 (6)	0.0102 (6)	0.0071 (6)
N3	0.0369 (7)	0.0382 (7)	0.0488 (8)	−0.0090 (6)	0.0146 (6)	0.0065 (6)
N4	0.0393 (7)	0.0368 (7)	0.0465 (8)	−0.0088 (6)	0.0163 (6)	0.0046 (6)
N5	0.0357 (7)	0.0383 (7)	0.0413 (7)	−0.0050 (5)	0.0139 (6)	0.0039 (6)
C1	0.0408 (8)	0.0461 (9)	0.0374 (8)	0.0006 (7)	0.0119 (7)	−0.0064 (7)
C2	0.0489 (10)	0.0551 (11)	0.0510 (10)	0.0109 (8)	0.0091 (8)	−0.0003 (9)
C3	0.0687 (13)	0.0524 (11)	0.0572 (11)	0.0101 (10)	0.0115 (10)	0.0121 (10)
C4	0.0680 (13)	0.0610 (12)	0.0575 (12)	−0.0006 (10)	0.0249 (10)	0.0158 (10)
C5	0.0469 (10)	0.0566 (11)	0.0510 (10)	0.0035 (8)	0.0206 (8)	0.0090 (9)
C6	0.0403 (8)	0.0435 (9)	0.0340 (8)	0.0006 (7)	0.0116 (6)	−0.0011 (7)
C7	0.0373 (10)	0.0740 (13)	0.0698 (13)	−0.0014 (9)	0.0162 (9)	−0.0158 (11)
C8	0.0399 (9)	0.0523 (10)	0.0457 (9)	0.0031 (7)	0.0208 (7)	0.0087 (8)
C9	0.0384 (9)	0.0479 (9)	0.0513 (10)	0.0024 (7)	0.0188 (7)	0.0068 (8)
C10	0.0394 (8)	0.0461 (9)	0.0380 (8)	−0.0102 (7)	0.0140 (7)	0.0000 (7)
C11	0.0431 (9)	0.0474 (9)	0.0376 (8)	−0.0020 (7)	0.0157 (7)	0.0006 (7)
C12	0.0367 (9)	0.0431 (9)	0.0485 (10)	−0.0124 (7)	0.0038 (7)	0.0081 (8)
C13	0.0344 (8)	0.0443 (9)	0.0453 (9)	−0.0033 (7)	0.0101 (7)	0.0122 (8)
C14	0.0375 (8)	0.0347 (8)	0.0366 (8)	−0.0046 (6)	0.0120 (6)	0.0058 (7)
C15	0.0457 (9)	0.0468 (9)	0.0474 (9)	−0.0047 (8)	0.0171 (8)	−0.0041 (8)
C16	0.0531 (11)	0.0473 (10)	0.0829 (15)	0.0033 (8)	0.0174 (10)	−0.0013 (10)
C17	0.0390 (8)	0.0335 (8)	0.0391 (8)	−0.0079 (6)	0.0154 (7)	0.0025 (7)
C18	0.0422 (9)	0.0618 (11)	0.0441 (9)	−0.0080 (8)	0.0109 (7)	0.0140 (9)
C19	0.0403 (10)	0.0835 (14)	0.0527 (11)	−0.0191 (10)	0.0079 (8)	0.0068 (11)
C20	0.0600 (12)	0.0545 (11)	0.0612 (12)	−0.0278 (9)	0.0280 (9)	−0.0116 (10)
C21	0.0615 (11)	0.0347 (8)	0.0530 (10)	−0.0109 (8)	0.0277 (9)	0.0040 (8)
C22	0.0487 (9)	0.0362 (8)	0.0393 (8)	−0.0065 (7)	0.0151 (7)	0.0033 (7)
C23	0.0579 (11)	0.0366 (9)	0.0684 (12)	−0.0104 (8)	0.0351 (9)	−0.0055 (9)
C24	0.0626 (12)	0.0443 (10)	0.0778 (14)	−0.0117 (9)	0.0464 (11)	−0.0081 (9)
C25	0.0698 (12)	0.0532 (11)	0.0568 (11)	−0.0191 (9)	0.0372 (10)	−0.0017 (9)
C26	0.0457 (11)	0.0653 (13)	0.1038 (18)	−0.0044 (9)	0.0356 (11)	0.0186 (13)

Geometric parameters (Å, º) top

S1—C13	1.6674 (18)	C11—H11B	0.9700
O1—C1	1.369 (2)	C12—H12B	0.98 (2)
O1—C7	1.423 (2)	C12—H12A	1.01 (2)
N1—C6	1.423 (2)	C14—C17	1.508 (2)
N1—C8	1.457 (2)	C15—C16	1.512 (3)
N1—C11	1.472 (2)	C15—H15A	0.9700
N2—C12	1.434 (2)	C15—H15B	0.9700
N2—C10	1.457 (2)	C16—H16A	0.9600
N2—C9	1.459 (2)	C16—H16B	0.9600
N3—C13	1.349 (2)	C16—H16C	0.9600
N3—N4	1.3790 (19)	C17—C23	1.538 (2)
N3—C12	1.472 (2)	C17—C22	1.539 (2)
N4—C14	1.305 (2)	C17—C18	1.545 (2)
N5—C13	1.378 (2)	C18—C19	1.532 (2)
N5—C14	1.383 (2)	C18—H18A	0.9700
N5—C15	1.470 (2)	C18—H18B	0.9700
C1—C2	1.383 (3)	C19—C20	1.524 (3)
C1—C6	1.413 (2)	C19—C26	1.529 (3)
C2—C3	1.378 (3)	C19—H19A	0.9800
C2—H2A	0.9300	C20—C21	1.520 (3)
C3—C4	1.362 (3)	C20—H20A	0.9700
C3—H3A	0.9300	C20—H20B	0.9700
C4—C5	1.385 (3)	C21—C25	1.519 (3)
C4—H4A	0.9300	C21—C22	1.525 (2)
C5—C6	1.390 (2)	C21—H21A	0.9800
C5—H5A	0.9300	C22—H22A	0.9700
C7—H7A	0.9600	C22—H22B	0.9700
C7—H7B	0.9600	C23—C24	1.538 (2)
C7—H7C	0.9600	C23—H23A	0.9700
C8—C9	1.513 (2)	C23—H23B	0.9700
C8—H8A	0.9700	C24—C25	1.519 (3)
C8—H8B	0.9700	C24—C26	1.526 (3)
C9—H9A	0.9700	C24—H24A	0.9800
C9—H9B	0.9700	C25—H25A	0.9700
C10—C11	1.513 (2)	C25—H25B	0.9700
C10—H10A	0.9700	C26—H26A	0.9700
C10—H10B	0.9700	C26—H26B	0.9700
C11—H11A	0.9700

C1—O1—C7	117.79 (15)	N5—C14—C17	127.20 (14)
C6—N1—C8	115.28 (13)	N5—C15—C16	112.40 (15)
C6—N1—C11	114.41 (13)	N5—C15—H15A	109.1
C8—N1—C11	110.33 (13)	C16—C15—H15A	109.1
C12—N2—C10	114.93 (14)	N5—C15—H15B	109.1
C12—N2—C9	114.58 (15)	C16—C15—H15B	109.1
C10—N2—C9	109.92 (13)	H15A—C15—H15B	107.9
C13—N3—N4	112.65 (13)	C15—C16—H16A	109.5
C13—N3—C12	126.97 (15)	C15—C16—H16B	109.5
N4—N3—C12	120.21 (15)	H16A—C16—H16B	109.5
C14—N4—N3	104.94 (13)	C15—C16—H16C	109.5
C13—N5—C14	108.06 (14)	H16A—C16—H16C	109.5
C13—N5—C15	120.98 (14)	H16B—C16—H16C	109.5
C14—N5—C15	130.96 (13)	C14—C17—C23	108.67 (13)
O1—C1—C2	123.40 (16)	C14—C17—C22	111.92 (13)
O1—C1—C6	116.34 (15)	C23—C17—C22	108.02 (14)
C2—C1—C6	120.23 (17)	C14—C17—C18	110.51 (13)
C3—C2—C1	121.06 (18)	C23—C17—C18	108.05 (15)
C3—C2—H2A	119.5	C22—C17—C18	109.55 (13)
C1—C2—H2A	119.5	C19—C18—C17	109.64 (14)
C4—C3—C2	119.73 (19)	C19—C18—H18A	109.7
C4—C3—H3A	120.1	C17—C18—H18A	109.7
C2—C3—H3A	120.1	C19—C18—H18B	109.7
C3—C4—C5	119.8 (2)	C17—C18—H18B	109.7
C3—C4—H4A	120.1	H18A—C18—H18B	108.2
C5—C4—H4A	120.1	C20—C19—C26	109.87 (17)
C4—C5—C6	122.32 (18)	C20—C19—C18	109.84 (17)
C4—C5—H5A	118.8	C26—C19—C18	109.18 (18)
C6—C5—H5A	118.8	C20—C19—H19A	109.3
C5—C6—C1	116.69 (16)	C26—C19—H19A	109.3
C5—C6—N1	123.09 (15)	C18—C19—H19A	109.3
C1—C6—N1	120.10 (15)	C21—C20—C19	109.41 (15)
O1—C7—H7A	109.5	C21—C20—H20A	109.8
O1—C7—H7B	109.5	C19—C20—H20A	109.8
H7A—C7—H7B	109.5	C21—C20—H20B	109.8
O1—C7—H7C	109.5	C19—C20—H20B	109.8
H7A—C7—H7C	109.5	H20A—C20—H20B	108.2
H7B—C7—H7C	109.5	C25—C21—C20	110.15 (17)
N1—C8—C9	111.00 (14)	C25—C21—C22	110.15 (15)
N1—C8—H8A	109.4	C20—C21—C22	109.18 (15)
C9—C8—H8A	109.4	C25—C21—H21A	109.1
N1—C8—H8B	109.4	C20—C21—H21A	109.1
C9—C8—H8B	109.4	C22—C21—H21A	109.1
H8A—C8—H8B	108.0	C21—C22—C17	110.05 (14)
N2—C9—C8	110.21 (15)	C21—C22—H22A	109.7
N2—C9—H9A	109.6	C17—C22—H22A	109.7
C8—C9—H9A	109.6	C21—C22—H22B	109.7
N2—C9—H9B	109.6	C17—C22—H22B	109.7
C8—C9—H9B	109.6	H22A—C22—H22B	108.2
H9A—C9—H9B	108.1	C17—C23—C24	110.33 (14)
N2—C10—C11	109.91 (13)	C17—C23—H23A	109.6
N2—C10—H10A	109.7	C24—C23—H23A	109.6
C11—C10—H10A	109.7	C17—C23—H23B	109.6
N2—C10—H10B	109.7	C24—C23—H23B	109.6
C11—C10—H10B	109.7	H23A—C23—H23B	108.1
H10A—C10—H10B	108.2	C25—C24—C26	109.76 (16)
N1—C11—C10	110.43 (14)	C25—C24—C23	109.57 (17)
N1—C11—H11A	109.6	C26—C24—C23	109.29 (17)
C10—C11—H11A	109.6	C25—C24—H24A	109.4
N1—C11—H11B	109.6	C26—C24—H24A	109.4
C10—C11—H11B	109.6	C23—C24—H24A	109.4
H11A—C11—H11B	108.1	C21—C25—C24	109.14 (15)
N2—C12—N3	116.71 (13)	C21—C25—H25A	109.9
N2—C12—H12B	113.0 (11)	C24—C25—H25A	109.9
N3—C12—H12B	103.6 (10)	C21—C25—H25B	109.9
N2—C12—H12A	108.6 (11)	C24—C25—H25B	109.9
N3—C12—H12A	106.1 (11)	H25A—C25—H25B	108.3
H12B—C12—H12A	108.5 (15)	C24—C26—C19	109.21 (16)
N3—C13—N5	103.80 (14)	C24—C26—H26A	109.8
N3—C13—S1	128.57 (13)	C19—C26—H26A	109.8
N5—C13—S1	127.63 (14)	C24—C26—H26B	109.8
N4—C14—N5	110.55 (13)	C19—C26—H26B	109.8
N4—C14—C17	122.24 (15)	H26A—C26—H26B	108.3

C13—N3—N4—C14	−0.07 (17)	N3—N4—C14—N5	0.16 (17)
C12—N3—N4—C14	−175.71 (14)	N3—N4—C14—C17	−178.86 (14)
C7—O1—C1—C2	10.9 (2)	C13—N5—C14—N4	−0.20 (18)
C7—O1—C1—C6	−167.17 (15)	C15—N5—C14—N4	179.95 (15)
O1—C1—C2—C3	−174.35 (18)	C13—N5—C14—C17	178.76 (15)
C6—C1—C2—C3	3.7 (3)	C15—N5—C14—C17	−1.1 (3)
C1—C2—C3—C4	−0.7 (3)	C13—N5—C15—C16	80.4 (2)
C2—C3—C4—C5	−2.0 (3)	C14—N5—C15—C16	−99.8 (2)
C3—C4—C5—C6	1.7 (3)	N4—C14—C17—C23	−8.7 (2)
C4—C5—C6—C1	1.2 (3)	N5—C14—C17—C23	172.44 (16)
C4—C5—C6—N1	177.19 (17)	N4—C14—C17—C22	−127.92 (16)
O1—C1—C6—C5	174.34 (15)	N5—C14—C17—C22	53.2 (2)
C2—C1—C6—C5	−3.8 (2)	N4—C14—C17—C18	109.70 (18)
O1—C1—C6—N1	−1.8 (2)	N5—C14—C17—C18	−69.2 (2)
C2—C1—C6—N1	−179.97 (15)	C14—C17—C18—C19	−178.89 (16)
C8—N1—C6—C5	−7.3 (2)	C23—C17—C18—C19	−60.1 (2)
C11—N1—C6—C5	122.18 (18)	C22—C17—C18—C19	57.4 (2)
C8—N1—C6—C1	168.57 (15)	C17—C18—C19—C20	−58.9 (2)
C11—N1—C6—C1	−61.93 (19)	C17—C18—C19—C26	61.6 (2)
C6—N1—C8—C9	−172.41 (14)	C26—C19—C20—C21	−59.0 (2)
C11—N1—C8—C9	56.12 (19)	C18—C19—C20—C21	61.1 (2)
C12—N2—C9—C8	−169.87 (13)	C19—C20—C21—C25	59.6 (2)
C10—N2—C9—C8	58.92 (17)	C19—C20—C21—C22	−61.5 (2)
N1—C8—C9—N2	−57.44 (18)	C25—C21—C22—C17	−60.62 (19)
C12—N2—C10—C11	169.35 (14)	C20—C21—C22—C17	60.46 (19)
C9—N2—C10—C11	−59.63 (17)	C14—C17—C22—C21	178.67 (14)
C6—N1—C11—C10	171.40 (13)	C23—C17—C22—C21	59.08 (18)
C8—N1—C11—C10	−56.68 (17)	C18—C17—C22—C21	−58.40 (18)
N2—C10—C11—N1	58.53 (17)	C14—C17—C23—C24	179.37 (15)
C10—N2—C12—N3	69.0 (2)	C22—C17—C23—C24	−59.0 (2)
C9—N2—C12—N3	−59.8 (2)	C18—C17—C23—C24	59.4 (2)
C13—N3—C12—N2	100.2 (2)	C17—C23—C24—C25	60.2 (2)
N4—N3—C12—N2	−84.8 (2)	C17—C23—C24—C26	−60.1 (2)
N4—N3—C13—N5	−0.05 (17)	C20—C21—C25—C24	−60.16 (19)
C12—N3—C13—N5	175.23 (14)	C22—C21—C25—C24	60.3 (2)
N4—N3—C13—S1	179.88 (12)	C26—C24—C25—C21	60.3 (2)
C12—N3—C13—S1	−4.8 (2)	C23—C24—C25—C21	−59.7 (2)
C14—N5—C13—N3	0.14 (17)	C25—C24—C26—C19	−60.0 (2)
C15—N5—C13—N3	−179.98 (13)	C23—C24—C26—C19	60.2 (2)
C14—N5—C13—S1	−179.79 (12)	C20—C19—C26—C24	59.2 (2)
C15—N5—C13—S1	0.1 (2)	C18—C19—C26—C24	−61.3 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1	0.97	2.26	2.903 (2)	123
C18—H18A···Cgⁱ	0.97	2.81	3.748 (2)	162

Symmetry code: (i) x−1, −y−1, z−1/2.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1	0.97	2.26	2.903 (2)	123
C18—H18A···Cgⁱ	0.97	2.81	3.748 (2)	162

Symmetry code: (i) x−1, −y−1, z−1/2.

Footnotes

‡Additonal correspondence author, e-mail: elemam5@hotmail.com.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center for Female Scientific and Medical Colleges, King Saud University, is greatly appreciated. CSCK thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

References

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

3-(Adamantan-1-yl)-4-ethyl-1-{[4-(2-meth­­oxy­phen­yl)piperazin-1-yl]meth­yl}-1H-1,2,4-triazole-5(4H)-thione

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organic compounds

3-(Adamantan-1-yl)-4-ethyl-1-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-1H-1,2,4-triazole-5(4H)-thione