organic compounds
3-(Adamantan-1-yl)-4-ethyl-1-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-1H-1,2,4-triazole-5(4H)-thione
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
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 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
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Data collection: APEX2 (Bruker, 2009); cell 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
https://doi.org/10.1107/S1600536813032789/rz5099sup1.cif
contains datablocks global, I. DOI: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
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).
The H atoms bound to atom C12 were located in a difference Fourier map and refined freely. All other H atoms were positioned geometrically [C—H = 0.93–1.01 Å] and refined using a riding model with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms. A rotating group model was used for the methyl groups.
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 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 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).
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,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).
Data collection: APEX2 (Bruker, 2009); cell
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).Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids. The intramolecular hydrogen bond is shown as a dashed line. |
C26H37N5OS | F(000) = 2016 |
Mr = 467.67 | Dx = 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 |
Bruker APEXII CCD diffractometer | 4029 independent reflections |
Radiation source: fine-focus sealed tube | 3606 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 65.0°, θmin = 4.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −22→23 |
Tmin = 0.344, Tmax = 0.599 | k = −9→14 |
15455 measured reflections | l = −25→21 |
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(Fo2) + (0.0627P)2 + 2.6908P] where P = (Fo2 + 2Fc2)/3 |
4029 reflections | (Δ/σ)max < 0.001 |
308 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C26H37N5OS | V = 4903.90 (17) Å3 |
Mr = 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)° |
Bruker APEXII CCD diffractometer | 4029 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3606 reflections with I > 2σ(I) |
Tmin = 0.344, Tmax = 0.599 | Rint = 0.033 |
15455 measured reflections |
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 | Δρmax = 0.19 e Å−3 |
4029 reflections | Δρmin = −0.27 e Å−3 |
308 parameters |
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 | 0.04659 (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)* |
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) |
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) |
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. |
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. |
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.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).