3-(Adamantan-1-yl)-1-[(4-ethyl­piperazin-1-yl)meth­yl]-4-[(E)-(4-hy­droxy­benzyl­idene)amino]-1H-1,2,4-triazole-5(4H)-thione

El-Emam, A.A.; Alrashood, K.A.; Al-Tamimi, A.-M.S.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812005107

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o657-o658

doi:10.1107/S1600536812005107

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3-(Adamantan-1-yl)-1-[(4-ethylpiperazin-1-yl)methyl]-4-[(E)-(4-hydroxybenzylidene)amino]-1H-1,2,4-triazole-5(4H)-thione

Ali A. El-Emam,^a ‡ Khalid A. Alrashood,^a Abdul-Malek S. Al-Tamimi,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 5 February 2012; accepted 6 February 2012; online 10 February 2012)

In the title thione, C₂₆H₃₆N₆OS, the 1,2,4-triazole ring is planar (r.m.s. deviation = 0.020 Å) and the benzene ring is twisted out of this plane [dihedral angle = 62.35 (12)°]. Supramolecular zigzag chains feature in the crystal packing. These are sustained by O—H⋯N(piperazine) hydrogen bonds, and are connected into the three-dimensional crystal structure by C—H⋯S and C—H⋯O interactions. The crystal studied was a racemic twin.

Related literature

For the biological activity of adamantyl derivatives, see: Vernier et al. (1969 ); El-Emam et al. (2004 ); Kadi et al. (2007 , 2010 ); Al-Omar et al. (2010 ). For related adamantane structures, see: Al-Tamimi et al. (2010 ); Kadi et al. (2011 ).

Experimental

Crystal data

C₂₆H₃₆N₆OS
M_r = 480.67
Monoclinic, C c
a = 16.1006 (6) Å
b = 14.2182 (5) Å
c = 11.4641 (4) Å
β = 92.440 (4)°
V = 2622.00 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.963, T_max = 0.977
12526 measured reflections
4840 independent reflections
4374 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.100
S = 1.03
4840 reflections
312 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), with 1811 Friedel pairs
Flack parameter: 0.06 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N6ⁱ	0.85 (1)	1.86 (1)	2.699 (3)	170 (5)
C13—H13B⋯S1ⁱⁱ	0.99	2.72	3.700 (2)	170
C22—H22⋯O1ⁱⁱⁱ	0.95	2.33	3.149 (3)	145
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+2, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812005107/hg5175sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005107/hg5175Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005107/hg5175Isup3.cml

checkCIF report

Comment top

Derivatives of adamantane have long been known for their diverse biological activities including anti-viral activity against the influenza (Vernier et al., 1969) and HIV viruses (El-Emam et al., 2004). Moreover, adamantane derivative were recently reported to exhibit marked anti-bacterial and anti-inflammatory activities (Kadi et al., 2007, 2010). In continuation of our interest in the chemical and pharmacological properties of adamantane derivatives, and as a part of on-going structural studies of adamantane derivatives (Kadi et al., 2011; Al-Tamimi et al., 2010) we synthesized the title compound (I) as potential chemotherapeutic agent.

The structure determination of (I), Fig. 1, confirms the presence of the thione in the solid-state. The central 1,2,4-triazole ring is planar [r.m.s. deviation = 0.020 Å] and the benzene ring is twisted out of this plane [dihedral angle = 62.35 (12)°]. Globally, the plane of the five-membered ring bisects the adamantyl group with the benzene and piperazine substituents lying to one side.

In the crystal packing, supramolecular zigzag chains are formed via O—H···N(piperazine) hydrogen bonds, Fig. 2 and Table 1. These are connected into the three-dimensional crystal structure by C—H···S and C—H···O interactions, Fig. 3 and Table 1.

Related literature top

For the biological activity of adamantyl derivatives, see: Vernier et al. (1969); El-Emam et al. (2004); Kadi et al. (2007, 2010); Al-Omar et al. (2010). For related adamantane structures, see: Al-Tamimi et al. (2010); Kadi et al. (2011).

Experimental top

A mixture of 709 mg (2 mmol) of 3-(1-adamantyl)-4-(4-hydroxybenzylideneamino)-4H-1,2,4-triazole-5-thiol (Al-Omar et al., 2010), 1-ethylpiperazine (228 mg, 2 mmol) and 37% formaldehyde solution (1 ml), in ethanol (8 ml) was heated under reflux for 15 min when 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 and the mixture was stirred for 20 min. The precipitated crude product were filtered, washed with water, dried, and crystallized from ethanol to yield 425 mg (44%) of the title compound (I) as colourless crystals. m.p. 436–438 K. ¹H NMR (CDCl₃): δ 1.18 (t, 3H, CH₃, J = 6.5 Hz), 1.69–1.76 (m, 6H, adamantane-H), 1.95 (s, 6H, adamantane-H), 2.03 (s, 3H, adamantane-H), 2.56 (q, 2H, CH₂CH₃, J = 6.5 Hz), 2.85–3.90 (m, 8H, piperazine-H), 5.18 (s, 2H, CH₂), 6.75 (d, 2H, Ar—H, J = 8.0 Hz), 7.67 (d, 2H, Ar—H, J = 8.0 Hz), 9.21 (s, 1H, CH═N). ¹³C NMR: δ 11.11 (CH₃), 27.84, 35.09, 36.48, 38.39 (adamantane-C), 49.50 (CH₂CH₃), 52.29, 58.43 (piperazine-C), 68.56 (CH₂), 116.53, 123.49, 130.87, 161.53 (Ar—C), 154.94 (triazole C-3), 163.34 (CH═N), 164.65 (C═ S).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the zigzag supramolecular chain along [100] in (I). The O—H···N hydrogen bonds are shown as orange dashed lines.
	Fig. 3. A view in projection down the c axis of the unit-cell contents for (I). The O—H···N, C—H···S and C—H···O interactions are shown as orange, brown and blue dashed lines, respectively.

3-(Adamantan-1-yl)-1-[(4-ethylpiperazin-1-yl)methyl]-4-[(E)-(4- hydroxybenzylidene)amino]-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₂₆H₃₆N₆OS	F(000) = 1032
M_r = 480.67	D_x = 1.218 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 4991 reflections
a = 16.1006 (6) Å	θ = 2.5–27.5°
b = 14.2182 (5) Å	µ = 0.15 mm⁻¹
c = 11.4641 (4) Å	T = 100 K
β = 92.440 (4)°	Prism, colourless
V = 2622.00 (16) Å³	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	4840 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4374 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.5°
ω scans	h = −20→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −18→18
T_min = 0.963, T_max = 0.977	l = −14→14
12526 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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0544P)² + 0.5109P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4840 reflections	Δρ_max = 0.25 e Å⁻³
312 parameters	Δρ_min = −0.18 e Å⁻³
3 restraints	Absolute structure: Flack (1983), with 1811 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (7)

Crystal data top

C₂₆H₃₆N₆OS	V = 2622.00 (16) Å³
M_r = 480.67	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 16.1006 (6) Å	µ = 0.15 mm⁻¹
b = 14.2182 (5) Å	T = 100 K
c = 11.4641 (4) Å	0.25 × 0.20 × 0.15 mm
β = 92.440 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	4840 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	4374 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.977	R_int = 0.036
12526 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	Δρ_max = 0.25 e Å⁻³
S = 1.03	Δρ_min = −0.18 e Å⁻³
4840 reflections	Absolute structure: Flack (1983), with 1811 Friedel pairs
312 parameters	Absolute structure parameter: 0.06 (7)
3 restraints

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

	x	y	z	U_iso*/U_eq
S1	0.49872 (4)	0.56121 (4)	0.50028 (4)	0.02603 (13)
O1	0.57958 (13)	1.01838 (13)	0.12630 (14)	0.0397 (5)
H1O	0.602 (3)	1.0657 (19)	0.160 (4)	0.103 (16)*
N1	0.38211 (12)	0.55968 (12)	0.66504 (16)	0.0249 (4)
N2	0.32689 (12)	0.61698 (13)	0.71956 (16)	0.0268 (4)
N3	0.38731 (11)	0.69230 (12)	0.57892 (15)	0.0201 (4)
N4	0.41828 (11)	0.77076 (12)	0.51938 (14)	0.0210 (4)
N5	0.32453 (12)	0.40404 (13)	0.71060 (16)	0.0257 (4)
N6	0.16089 (12)	0.32789 (13)	0.70910 (17)	0.0292 (4)
C1	0.28270 (14)	0.78354 (15)	0.69923 (18)	0.0244 (5)
C2	0.34125 (17)	0.85912 (18)	0.7529 (2)	0.0387 (6)
H2A	0.3724	0.8331	0.8219	0.046*
H2B	0.3818	0.8788	0.6952	0.046*
C3	0.2896 (2)	0.9442 (2)	0.7892 (3)	0.0545 (9)
H3	0.3275	0.9931	0.8245	0.065*
C4	0.2445 (2)	0.98457 (18)	0.6805 (3)	0.0486 (8)
H4A	0.2134	1.0418	0.7014	0.058*
H4B	0.2853	1.0021	0.6221	0.058*
C5	0.18436 (17)	0.91073 (17)	0.6291 (2)	0.0350 (6)
H5	0.1535	0.9376	0.5593	0.042*
C6	0.12260 (17)	0.88242 (19)	0.7202 (2)	0.0409 (6)
H6A	0.0906	0.9382	0.7439	0.049*
H6B	0.0829	0.8356	0.6864	0.049*
C7	0.1689 (2)	0.8407 (2)	0.8263 (2)	0.0474 (8)
H7	0.1281	0.8216	0.8853	0.057*
C8	0.2276 (2)	0.9136 (3)	0.8790 (3)	0.0678 (12)
H8A	0.2579	0.8870	0.9483	0.081*
H8B	0.1956	0.9688	0.9045	0.081*
C9	0.21912 (18)	0.75416 (19)	0.7898 (2)	0.0408 (7)
H9A	0.1810	0.7059	0.7556	0.049*
H9B	0.2486	0.7266	0.8592	0.049*
C10	0.23419 (15)	0.82507 (16)	0.5923 (2)	0.0281 (5)
H10A	0.2735	0.8437	0.5323	0.034*
H10B	0.1961	0.7770	0.5578	0.034*
C11	0.33174 (14)	0.69771 (15)	0.66707 (18)	0.0231 (4)
C12	0.42254 (13)	0.60297 (14)	0.58011 (18)	0.0205 (4)
C13	0.39656 (14)	0.46264 (15)	0.7065 (2)	0.0273 (5)
H13A	0.4365	0.4323	0.6551	0.033*
H13B	0.4232	0.4655	0.7859	0.033*
C14	0.27018 (14)	0.42163 (15)	0.80734 (18)	0.0240 (5)
H14A	0.2378	0.4799	0.7926	0.029*
H14B	0.3039	0.4297	0.8809	0.029*
C15	0.21187 (14)	0.33867 (16)	0.8179 (2)	0.0278 (5)
H15A	0.2445	0.2806	0.8333	0.033*
H15B	0.1754	0.3489	0.8841	0.033*
C16	0.21480 (17)	0.31573 (17)	0.6094 (2)	0.0353 (6)
H16A	0.1800	0.3122	0.5363	0.042*
H16B	0.2457	0.2558	0.6184	0.042*
C17	0.27601 (17)	0.39628 (17)	0.6011 (2)	0.0323 (5)
H17A	0.3134	0.3847	0.5362	0.039*
H17B	0.2456	0.4557	0.5850	0.039*
C18	0.10554 (18)	0.24398 (19)	0.7131 (3)	0.0436 (7)
H18A	0.1404	0.1868	0.7211	0.052*
H18B	0.0729	0.2393	0.6381	0.052*
C19	0.04676 (18)	0.2464 (2)	0.8111 (3)	0.0496 (7)
H19A	0.0136	0.1886	0.8101	0.074*
H19B	0.0098	0.3009	0.8014	0.074*
H19C	0.0785	0.2514	0.8857	0.074*
C20	0.42424 (13)	0.75687 (15)	0.40960 (18)	0.0211 (4)
H20	0.4039	0.7001	0.3753	0.025*
C21	0.46203 (13)	0.82785 (14)	0.33739 (18)	0.0213 (4)
C22	0.50449 (14)	0.90456 (15)	0.38680 (19)	0.0250 (5)
H22	0.5069	0.9122	0.4692	0.030*
C23	0.54296 (15)	0.96938 (15)	0.31823 (19)	0.0267 (5)
H23	0.5711	1.0216	0.3534	0.032*
C24	0.54077 (15)	0.95855 (17)	0.19726 (19)	0.0284 (5)
C25	0.49716 (16)	0.88341 (18)	0.1466 (2)	0.0325 (6)
H25	0.4938	0.8768	0.0640	0.039*
C26	0.45868 (15)	0.81838 (16)	0.21584 (18)	0.0275 (5)
H26	0.4297	0.7668	0.1806	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0246 (3)	0.0275 (2)	0.0267 (3)	0.0066 (2)	0.0095 (2)	0.0022 (2)
O1	0.0465 (12)	0.0445 (10)	0.0276 (9)	−0.0220 (9)	−0.0034 (8)	0.0134 (8)
N1	0.0260 (10)	0.0223 (9)	0.0272 (9)	0.0052 (8)	0.0092 (8)	0.0052 (7)
N2	0.0282 (10)	0.0265 (9)	0.0266 (9)	0.0083 (8)	0.0129 (8)	0.0063 (8)
N3	0.0206 (9)	0.0206 (8)	0.0196 (8)	0.0011 (7)	0.0060 (7)	0.0006 (7)
N4	0.0205 (9)	0.0217 (8)	0.0212 (9)	−0.0005 (7)	0.0042 (7)	0.0046 (7)
N5	0.0257 (10)	0.0230 (9)	0.0288 (9)	0.0039 (8)	0.0056 (8)	0.0029 (8)
N6	0.0253 (11)	0.0304 (10)	0.0319 (10)	0.0012 (8)	0.0030 (8)	−0.0066 (8)
C1	0.0272 (12)	0.0259 (11)	0.0206 (10)	0.0077 (9)	0.0068 (9)	0.0033 (9)
C2	0.0395 (15)	0.0363 (13)	0.0396 (14)	0.0138 (12)	−0.0057 (12)	−0.0131 (12)
C3	0.0535 (19)	0.0411 (16)	0.068 (2)	0.0176 (14)	−0.0071 (17)	−0.0274 (15)
C4	0.0480 (18)	0.0238 (12)	0.075 (2)	0.0142 (12)	0.0164 (15)	0.0012 (13)
C5	0.0321 (14)	0.0366 (12)	0.0369 (14)	0.0157 (11)	0.0105 (11)	0.0127 (11)
C6	0.0364 (15)	0.0418 (14)	0.0459 (15)	0.0190 (12)	0.0185 (12)	0.0127 (12)
C7	0.0552 (19)	0.0547 (17)	0.0344 (14)	0.0306 (15)	0.0245 (13)	0.0088 (13)
C8	0.083 (3)	0.082 (2)	0.0383 (16)	0.057 (2)	0.0067 (17)	−0.0153 (16)
C9	0.0424 (16)	0.0485 (15)	0.0334 (13)	0.0243 (13)	0.0248 (12)	0.0166 (12)
C10	0.0256 (12)	0.0369 (12)	0.0223 (10)	0.0081 (10)	0.0054 (9)	0.0047 (10)
C11	0.0249 (11)	0.0261 (10)	0.0186 (10)	0.0036 (9)	0.0059 (8)	0.0043 (9)
C12	0.0196 (11)	0.0219 (10)	0.0200 (10)	0.0016 (8)	0.0005 (8)	−0.0004 (9)
C13	0.0249 (12)	0.0245 (10)	0.0332 (12)	0.0062 (9)	0.0083 (10)	0.0106 (10)
C14	0.0236 (12)	0.0257 (10)	0.0226 (10)	0.0018 (9)	0.0012 (9)	0.0021 (9)
C15	0.0223 (12)	0.0295 (11)	0.0318 (12)	0.0020 (9)	0.0035 (10)	0.0037 (10)
C16	0.0367 (15)	0.0345 (12)	0.0348 (13)	0.0057 (11)	0.0028 (11)	−0.0121 (11)
C17	0.0391 (15)	0.0321 (12)	0.0261 (11)	0.0082 (10)	0.0043 (10)	−0.0020 (10)
C18	0.0300 (15)	0.0367 (13)	0.0640 (18)	−0.0040 (11)	0.0005 (13)	−0.0110 (13)
C19	0.0297 (15)	0.0518 (16)	0.067 (2)	−0.0095 (13)	0.0024 (14)	−0.0083 (15)
C20	0.0181 (11)	0.0201 (9)	0.0252 (11)	0.0008 (8)	0.0032 (8)	0.0020 (8)
C21	0.0189 (11)	0.0234 (10)	0.0217 (10)	0.0012 (8)	0.0027 (8)	0.0042 (9)
C22	0.0260 (12)	0.0276 (10)	0.0216 (10)	−0.0014 (9)	0.0018 (9)	0.0015 (9)
C23	0.0282 (12)	0.0243 (10)	0.0274 (11)	−0.0080 (9)	0.0001 (10)	0.0027 (9)
C24	0.0262 (12)	0.0323 (12)	0.0265 (11)	−0.0065 (9)	−0.0002 (10)	0.0103 (9)
C25	0.0362 (15)	0.0405 (13)	0.0206 (10)	−0.0119 (11)	−0.0007 (10)	0.0054 (10)
C26	0.0286 (13)	0.0293 (11)	0.0246 (11)	−0.0078 (10)	0.0020 (10)	0.0002 (9)

Geometric parameters (Å, º) top

S1—C12	1.670 (2)	C7—H7	1.0000
O1—C24	1.349 (3)	C8—H8A	0.9900
O1—H1O	0.850 (10)	C8—H8B	0.9900
N1—C12	1.343 (3)	C9—H9A	0.9900
N1—N2	1.376 (3)	C9—H9B	0.9900
N1—C13	1.475 (3)	C10—H10A	0.9900
N2—C11	1.300 (3)	C10—H10B	0.9900
N3—C11	1.380 (3)	C13—H13A	0.9900
N3—C12	1.391 (3)	C13—H13B	0.9900
N3—N4	1.410 (2)	C14—C15	1.516 (3)
N4—C20	1.282 (3)	C14—H14A	0.9900
N5—C13	1.430 (3)	C14—H14B	0.9900
N5—C17	1.455 (3)	C15—H15A	0.9900
N5—C14	1.463 (3)	C15—H15B	0.9900
N6—C15	1.472 (3)	C16—C17	1.517 (4)
N6—C16	1.474 (3)	C16—H16A	0.9900
N6—C18	1.491 (3)	C16—H16B	0.9900
C1—C11	1.508 (3)	C17—H17A	0.9900
C1—C10	1.543 (3)	C17—H17B	0.9900
C1—C2	1.540 (3)	C18—C19	1.500 (4)
C1—C9	1.547 (3)	C18—H18A	0.9900
C2—C3	1.535 (3)	C18—H18B	0.9900
C2—H2A	0.9900	C19—H19A	0.9800
C2—H2B	0.9900	C19—H19B	0.9800
C3—C8	1.527 (6)	C19—H19C	0.9800
C3—C4	1.527 (4)	C20—C21	1.455 (3)
C3—H3	1.0000	C20—H20	0.9500
C4—C5	1.529 (4)	C21—C22	1.395 (3)
C4—H4A	0.9900	C21—C26	1.399 (3)
C4—H4B	0.9900	C22—C23	1.376 (3)
C5—C6	1.527 (4)	C22—H22	0.9500
C5—C10	1.528 (3)	C23—C24	1.394 (3)
C5—H5	1.0000	C23—H23	0.9500
C6—C7	1.519 (4)	C24—C25	1.392 (3)
C6—H6A	0.9900	C25—C26	1.382 (3)
C6—H6B	0.9900	C25—H25	0.9500
C7—C8	1.512 (5)	C26—H26	0.9500
C7—C9	1.540 (3)

C24—O1—H1O	115 (3)	C5—C10—H10B	109.7
C12—N1—N2	113.61 (17)	C1—C10—H10B	109.7
C12—N1—C13	126.00 (18)	H10A—C10—H10B	108.2
N2—N1—C13	120.25 (18)	N2—C11—N3	110.08 (19)
C11—N2—N1	105.06 (18)	N2—C11—C1	124.0 (2)
C11—N3—C12	108.69 (17)	N3—C11—C1	125.92 (19)
C11—N3—N4	124.34 (18)	N1—C12—N3	102.45 (18)
C12—N3—N4	125.08 (18)	N1—C12—S1	128.61 (15)
C20—N4—N3	113.35 (17)	N3—C12—S1	128.90 (16)
C13—N5—C17	114.98 (19)	N5—C13—N1	116.01 (18)
C13—N5—C14	115.93 (18)	N5—C13—H13A	108.3
C17—N5—C14	110.53 (18)	N1—C13—H13A	108.3
C15—N6—C16	110.09 (18)	N5—C13—H13B	108.3
C15—N6—C18	111.71 (19)	N1—C13—H13B	108.3
C16—N6—C18	107.59 (19)	H13A—C13—H13B	107.4
C11—C1—C10	111.59 (18)	N5—C14—C15	108.67 (18)
C11—C1—C2	110.14 (19)	N5—C14—H14A	110.0
C10—C1—C2	109.34 (19)	C15—C14—H14A	110.0
C11—C1—C9	108.30 (18)	N5—C14—H14B	110.0
C10—C1—C9	108.06 (19)	C15—C14—H14B	110.0
C2—C1—C9	109.3 (2)	H14A—C14—H14B	108.3
C3—C2—C1	109.2 (2)	N6—C15—C14	109.78 (18)
C3—C2—H2A	109.8	N6—C15—H15A	109.7
C1—C2—H2A	109.8	C14—C15—H15A	109.7
C3—C2—H2B	109.8	N6—C15—H15B	109.7
C1—C2—H2B	109.8	C14—C15—H15B	109.7
H2A—C2—H2B	108.3	H15A—C15—H15B	108.2
C8—C3—C4	110.8 (3)	N6—C16—C17	111.47 (19)
C8—C3—C2	109.6 (3)	N6—C16—H16A	109.3
C4—C3—C2	108.6 (2)	C17—C16—H16A	109.3
C8—C3—H3	109.3	N6—C16—H16B	109.3
C4—C3—H3	109.3	C17—C16—H16B	109.3
C2—C3—H3	109.3	H16A—C16—H16B	108.0
C5—C4—C3	109.1 (2)	N5—C17—C16	109.2 (2)
C5—C4—H4A	109.9	N5—C17—H17A	109.8
C3—C4—H4A	109.9	C16—C17—H17A	109.8
C5—C4—H4B	109.9	N5—C17—H17B	109.8
C3—C4—H4B	109.9	C16—C17—H17B	109.8
H4A—C4—H4B	108.3	H17A—C17—H17B	108.3
C6—C5—C10	110.1 (2)	N6—C18—C19	113.7 (2)
C6—C5—C4	109.7 (2)	N6—C18—H18A	108.8
C10—C5—C4	108.8 (2)	C19—C18—H18A	108.8
C6—C5—H5	109.4	N6—C18—H18B	108.8
C10—C5—H5	109.4	C19—C18—H18B	108.8
C4—C5—H5	109.4	H18A—C18—H18B	107.7
C7—C6—C5	109.8 (2)	C18—C19—H19A	109.5
C7—C6—H6A	109.7	C18—C19—H19B	109.5
C5—C6—H6A	109.7	H19A—C19—H19B	109.5
C7—C6—H6B	109.7	C18—C19—H19C	109.5
C5—C6—H6B	109.7	H19A—C19—H19C	109.5
H6A—C6—H6B	108.2	H19B—C19—H19C	109.5
C8—C7—C6	109.2 (3)	N4—C20—C21	120.16 (19)
C8—C7—C9	109.3 (3)	N4—C20—H20	119.9
C6—C7—C9	109.9 (2)	C21—C20—H20	119.9
C8—C7—H7	109.5	C22—C21—C26	118.51 (19)
C6—C7—H7	109.5	C22—C21—C20	121.40 (19)
C9—C7—H7	109.5	C26—C21—C20	120.05 (19)
C7—C8—C3	109.9 (2)	C23—C22—C21	121.1 (2)
C7—C8—H8A	109.7	C23—C22—H22	119.4
C3—C8—H8A	109.7	C21—C22—H22	119.4
C7—C8—H8B	109.7	C22—C23—C24	120.1 (2)
C3—C8—H8B	109.7	C22—C23—H23	120.0
H8A—C8—H8B	108.2	C24—C23—H23	120.0
C7—C9—C1	109.7 (2)	O1—C24—C25	118.1 (2)
C7—C9—H9A	109.7	O1—C24—C23	122.5 (2)
C1—C9—H9A	109.7	C25—C24—C23	119.4 (2)
C7—C9—H9B	109.7	C26—C25—C24	120.3 (2)
C1—C9—H9B	109.7	C26—C25—H25	119.9
H9A—C9—H9B	108.2	C24—C25—H25	119.9
C5—C10—C1	109.84 (19)	C25—C26—C21	120.6 (2)
C5—C10—H10A	109.7	C25—C26—H26	119.7
C1—C10—H10A	109.7	C21—C26—H26	119.7

C12—N1—N2—C11	0.8 (2)	C10—C1—C11—N3	52.9 (3)
C13—N1—N2—C11	176.73 (19)	C2—C1—C11—N3	−68.8 (3)
C11—N3—N4—C20	−140.2 (2)	C9—C1—C11—N3	171.7 (2)
C12—N3—N4—C20	57.3 (3)	N2—N1—C12—N3	−2.5 (2)
C11—C1—C2—C3	−177.9 (2)	C13—N1—C12—N3	−178.14 (19)
C10—C1—C2—C3	59.2 (3)	N2—N1—C12—S1	175.18 (16)
C9—C1—C2—C3	−59.0 (3)	C13—N1—C12—S1	−0.5 (3)
C1—C2—C3—C8	60.0 (3)	C11—N3—C12—N1	3.2 (2)
C1—C2—C3—C4	−61.2 (3)	N4—N3—C12—N1	168.07 (18)
C8—C3—C4—C5	−57.6 (3)	C11—N3—C12—S1	−174.48 (16)
C2—C3—C4—C5	62.8 (3)	N4—N3—C12—S1	−9.6 (3)
C3—C4—C5—C6	58.3 (3)	C17—N5—C13—N1	55.3 (3)
C3—C4—C5—C10	−62.2 (3)	C14—N5—C13—N1	−75.8 (2)
C10—C5—C6—C7	59.2 (3)	C12—N1—C13—N5	−128.4 (2)
C4—C5—C6—C7	−60.5 (3)	N2—N1—C13—N5	56.2 (3)
C5—C6—C7—C8	60.8 (3)	C13—N5—C14—C15	−164.70 (17)
C5—C6—C7—C9	−59.0 (3)	C17—N5—C14—C15	62.2 (2)
C6—C7—C8—C3	−59.5 (3)	C16—N6—C15—C14	57.6 (2)
C9—C7—C8—C3	60.8 (3)	C18—N6—C15—C14	177.0 (2)
C4—C3—C8—C7	58.6 (3)	N5—C14—C15—N6	−60.5 (2)
C2—C3—C8—C7	−61.2 (3)	C15—N6—C16—C17	−55.8 (2)
C8—C7—C9—C1	−59.7 (3)	C18—N6—C16—C17	−177.7 (2)
C6—C7—C9—C1	60.1 (3)	C13—N5—C17—C16	166.65 (19)
C11—C1—C9—C7	179.0 (2)	C14—N5—C17—C16	−59.7 (2)
C10—C1—C9—C7	−59.9 (3)	N6—C16—C17—N5	56.4 (2)
C2—C1—C9—C7	59.0 (3)	C15—N6—C18—C19	59.0 (3)
C6—C5—C10—C1	−60.2 (3)	C16—N6—C18—C19	179.9 (2)
C4—C5—C10—C1	60.1 (3)	N3—N4—C20—C21	−174.54 (17)
C11—C1—C10—C5	179.1 (2)	N4—C20—C21—C22	10.6 (3)
C2—C1—C10—C5	−58.8 (3)	N4—C20—C21—C26	−171.5 (2)
C9—C1—C10—C5	60.1 (3)	C26—C21—C22—C23	−0.5 (3)
N1—N2—C11—N3	1.3 (2)	C20—C21—C22—C23	177.3 (2)
N1—N2—C11—C1	−179.0 (2)	C21—C22—C23—C24	−0.7 (4)
C12—N3—C11—N2	−3.0 (2)	C22—C23—C24—O1	−177.9 (2)
N4—N3—C11—N2	−167.98 (19)	C22—C23—C24—C25	2.0 (4)
C12—N3—C11—C1	177.3 (2)	O1—C24—C25—C26	177.8 (2)
N4—N3—C11—C1	12.3 (3)	C23—C24—C25—C26	−2.1 (4)
C10—C1—C11—N2	−126.8 (2)	C24—C25—C26—C21	0.9 (4)
C2—C1—C11—N2	111.6 (3)	C22—C21—C26—C25	0.4 (3)
C9—C1—C11—N2	−8.0 (3)	C20—C21—C26—C25	−177.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N6ⁱ	0.85 (1)	1.86 (1)	2.699 (3)	170 (5)
C13—H13B···S1ⁱⁱ	0.99	2.72	3.700 (2)	170
C22—H22···O1ⁱⁱⁱ	0.95	2.33	3.149 (3)	145

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x, −y+1, z+1/2; (iii) x, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₃₆N₆OS
M_r	480.67
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	16.1006 (6), 14.2182 (5), 11.4641 (4)
β (°)	92.440 (4)
V (Å³)	2622.00 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.963, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	12526, 4840, 4374
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.100, 1.03
No. of reflections	4840
No. of parameters	312
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)	0.25, −0.18
Absolute structure	Flack (1983), with 1811 Friedel pairs
Absolute structure parameter	0.06 (7)

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N6ⁱ	0.85 (1)	1.86 (1)	2.699 (3)	170 (5)
C13—H13B···S1ⁱⁱ	0.99	2.72	3.700 (2)	170
C22—H22···O1ⁱⁱⁱ	0.95	2.33	3.149 (3)	145

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x, −y+1, z+1/2; (iii) x, −y+2, z+1/2.

Footnotes

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

Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University is greatly appreciated. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research Scheme (grant No. UM.C/HIR/MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Al-Omar, M. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Molecules, 15, 2526–2550. Web of Science CAS PubMed Google Scholar
Al-Tamimi, A.-M. S., Bari, A., Al-Omar, M. A., Alrashood, K. A. & El-Emam, A. A. (2010). Acta Cryst. E66, o1756. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107–5113. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kadi, A. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Eur. J. Med. Chem. 45, 5006–5011. Web of Science CrossRef CAS PubMed Google Scholar
Kadi, A. A., Alanzi, A. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o3127. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235–242. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vernier, V. G., Harmon, J. B., Stump, J. M., Lynes, T. L., Marvel, M. P. & Smith, D. H. (1969). Toxicol. Appl. Pharmacol. 15, 642–665. CrossRef CAS PubMed Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Pages o657-o658

doi:10.1107/S1600536812005107

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

3-(Adamantan-1-yl)-1-[(4-ethyl­piperazin-1-yl)meth­yl]-4-[(E)-(4-hy­dr­oxy­benzyl­­idene)amino]-1H-1,2,4-triazole-5(4H)-thione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

3-(Adamantan-1-yl)-1-[(4-ethylpiperazin-1-yl)methyl]-4-[(E)-(4-hydroxybenzylidene)amino]-1H-1,2,4-triazole-5(4H)-thione