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

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

doi:10.1107/S1600536812021204

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1766-o1767

doi:10.1107/S1600536812021204

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

Ali A. El-Emam,^a ‡ Mohamed A. Al-Omar,^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 8 May 2012; accepted 10 May 2012; online 19 May 2012)

In the title compound, C₃₁H₃₈N₆OS, the conformation about the N=C [1.285 (2) Å] imine bond is E. The piperazine ring has a chair conformation and occupies a position almost perpendicular to the plane through the triazole ring; the benzene ring forms a dihedral angle of 31.95 (10)° with the triazole ring. Overall, the molecule has the shape of a flattened bowl. The hydroxy group is disordered over two positions. The major component has a site-occupancy factor of 0.762 (3) and forms an intramolecular O—H⋯N(imine) bond to close an S(6) loop. The minor component of the disordered hydroxy group forms an O—H⋯N(piperazine) hydrogen bond. These, along with C—H⋯S and C—H⋯N interactions, link molecules into a three-dimensional architecture.

Related literature

For the diverse biological activities of adamantane derivatives, see: Vernier et al. (1969 ); El-Emam et al. (2004 ); Kadi et al. (2007 , 2010 ). For related structural studies, see: Kadi et al. (2011 ); El-Emam et al. (2012 ). For the synthesis of the precursor to the title compound, see: Al-Omar et al. (2010 )

Experimental

Crystal data

C₃₁H₃₈N₆OS
M_r = 542.73
Monoclinic, P 2₁ /n
a = 10.6015 (5) Å
b = 12.0283 (7) Å
c = 22.7865 (12) Å
β = 101.222 (4)°
V = 2850.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 100 K
0.40 × 0.40 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.570, T_max = 1.000
11447 measured reflections
6530 independent reflections
4526 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.125
S = 1.02
6530 reflections
364 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.84	1.89	2.632 (2)	147
O1′—H1o′⋯N5ⁱ	0.84	1.92	2.714 (6)	158
C13—H13A⋯S1ⁱⁱ	0.99	2.68	3.650 (2)	166
C30—H30⋯N6ⁱⁱⁱ	0.95	2.54	3.484 (3)	172
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536812021204/qm2068sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021204/qm2068Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021204/qm2068Isup3.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 derivatives were reported to exhibit marked anti-bacterial and anti-inflammatory activities (Kadi et al., 2007; Kadi et al., 2010). In continuation of our interest in the chemical and pharmacological properties of adamantane derivatives, and as part of on-going structural studies (Kadi et al., 2011; El-Emam et al., 2012), we synthesized the title compound (I) as a potential chemotherapeutic agent. Herein, we describe the crystal and molecular structure of (I).

In (I), Fig. 1, the conformation about the N1═C25 [1.285 (2) Å] imine bond is E. The piperazinyl ring, having a chair conformation, projects almost normal to the plane through the triazole ring (r.m.s. deviation = 0.014 Å) as seen in the value of the N3—N4—C13—N5 torsion angle = -67.3 (2)°. By contrast, the benzene ring is splayed with respect to the triazole ring with the C25—N1—N2—C11 torsion angle being -153.92 (17)°; the dihedral angle between the rings is 31.95 (10)°. Overall, the molecule has the shape of a flattened bowl. As noted below, the hydroxy group is disordered over two positions. The major component is aligned to allow the formation of an intramolecular O—H···N(imine) bond to close an S(6) loop, Table 1.

In the crystal packing, the minor component of the disordered hydroxy group forms an O—H···N(piperazinyl) hydrogen bond; Table 1. Additional links between molecules are of the type C—H···S and C—H···N, Table 1, to consolidate the crystal packing, Fig. 2.

Related literature top

For the diverse biological activities of adamantane derivatives, see: Vernier et al. (1969); El-Emam et al. (2004); Kadi et al. (2007, 2010). For related structural studies, see: Kadi et al. (2011); El-Emam et al. (2012). For the synthesis of the precursor to the title compound, see: Al-Omar et al. (2010)

Experimental top

A mixture of 3-(1-adamantyl)-4-(2-hydroxybenzylideneamino)-4H-1,2,4-triazole-5-thiol (709 mg, 2 mmol), prepared following literature methods (Al-Omar et al., 2010), 1-benzylpiperazine (353 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 was filtered, washed with water, dried, and crystallized from ethanol to yield 413 mg (38%) of the title compound as colourless crystals. M.pt: 437–439 K. Crystals were obtained by slow evaporation of its CHCl₃:EtOH (1:1; 5 ml) solution at room temperature. ¹H NMR (DMSO-d₆, 500.13 MHz): δ 1.71 (br. s, 6H, adamantane-H), 2.04 (s, 3H, adamantane-H), 2.09 (s, 6H, adamantane-H), 2.37 (br. s, 4H, piperazine-H), 2.72 (s, 4H, piperazine-H), 3.49 (s, 2H, PhCH₂), 5.16 (s, 2H, CH₂), 6.98–7.03 (m, 2H, Ar—H), 7.23–7.32 (m, 5H, Ar—H), 7.44–7.47 (m, 2H, Ar—H), 9.85 (s, 1H, CH═ N), 10.50 (br. s, 1H, OH) p.p.m. ¹³C NMR (DMSO-d₆, 125.76 MHz): δ 27.18, 34.73, 35.92, 38.10 (adamantane-C), 49.93, 52.47 (piperazine-C), 62.08 (PhCH₂), 68.69 (CH₂), 116.77, 118.28, 119.80, 126.68, 126.85, 128.09, 128.82, 134.44, 138.01, 158.56 (Ar—C), 154.20 (triazole C-5), 162.01 p.p.m.

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 in projection down the b axis of the unit-cell contents for (I). The O—H···S, C—H···S and C—H···N are shown as blue, orange, and purple dashed lines, respectively.

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

Crystal data top

C₃₁H₃₈N₆OS	F(000) = 1160
M_r = 542.73	D_x = 1.265 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3530 reflections
a = 10.6015 (5) Å	θ = 2.3–27.5°
b = 12.0283 (7) Å	µ = 0.15 mm⁻¹
c = 22.7865 (12) Å	T = 100 K
β = 101.222 (4)°	Prism, colourless
V = 2850.1 (3) Å³	0.40 × 0.40 × 0.10 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	6530 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4526 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.032
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.3°
ω scan	h = −13→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→15
T_min = 0.570, T_max = 1.000	l = −20→29
11447 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.042P)² + 0.843P] where P = (F_o² + 2F_c²)/3
6530 reflections	(Δ/σ)_max = 0.001
364 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₃₁H₃₈N₆OS	V = 2850.1 (3) Å³
M_r = 542.73	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.6015 (5) Å	µ = 0.15 mm⁻¹
b = 12.0283 (7) Å	T = 100 K
c = 22.7865 (12) Å	0.40 × 0.40 × 0.10 mm
β = 101.222 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	6530 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	4526 reflections with I > 2σ(I)
T_min = 0.570, T_max = 1.000	R_int = 0.032
11447 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.02	Δρ_max = 0.28 e Å⁻³
6530 reflections	Δρ_min = −0.29 e Å⁻³
364 parameters

Special details top

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	Occ. (<1)
S1	0.26003 (5)	0.62548 (5)	0.73271 (3)	0.03659 (16)
O1	0.67165 (14)	0.49724 (17)	0.61888 (8)	0.0329 (6)	0.762 (3)
H1o	0.6498	0.5466	0.6410	0.049*	0.762 (3)
O1'	0.2282 (5)	0.4574 (5)	0.5670 (3)	0.0324 (18)	0.238 (3)
H1o'	0.1859	0.4049	0.5780	0.049*	0.238 (3)
N1	0.51345 (13)	0.62441 (13)	0.66474 (7)	0.0240 (4)
N2	0.48195 (13)	0.70959 (13)	0.70132 (7)	0.0222 (3)
N3	0.51922 (14)	0.86006 (14)	0.75723 (7)	0.0261 (4)
N4	0.40900 (13)	0.80618 (14)	0.76589 (7)	0.0265 (4)
N5	0.41461 (14)	0.82682 (15)	0.87387 (7)	0.0280 (4)
N6	0.61744 (15)	0.77152 (15)	0.97143 (7)	0.0307 (4)
C1	0.68951 (16)	0.82020 (17)	0.69971 (8)	0.0229 (4)
C2	0.74105 (17)	0.93454 (18)	0.72398 (9)	0.0290 (4)
H2A	0.6806	0.9936	0.7061	0.035*
H2B	0.7479	0.9366	0.7679	0.035*
C3	0.87413 (18)	0.95560 (19)	0.70855 (9)	0.0351 (5)
H3	0.9070	1.0298	0.7245	0.042*
C4	0.8622 (2)	0.9539 (2)	0.64047 (9)	0.0386 (5)
H4A	0.8029	1.0133	0.6221	0.046*
H4B	0.9474	0.9677	0.6302	0.046*
C5	0.81110 (19)	0.84063 (19)	0.61607 (9)	0.0348 (5)
H5	0.8038	0.8395	0.5716	0.042*
C6	0.67807 (17)	0.82016 (18)	0.63125 (8)	0.0278 (4)
H6A	0.6439	0.7477	0.6146	0.033*
H6B	0.6177	0.8792	0.6132	0.033*
C7	0.78629 (16)	0.73016 (18)	0.72866 (9)	0.0281 (4)
H7A	0.7946	0.7321	0.7727	0.034*
H7B	0.7543	0.6557	0.7144	0.034*
C8	0.91771 (17)	0.7508 (2)	0.71237 (10)	0.0364 (5)
H8	0.9793	0.6915	0.7304	0.044*
C9	0.90309 (18)	0.7490 (2)	0.64414 (10)	0.0380 (5)
H9A	0.9881	0.7602	0.6332	0.046*
H9B	0.8695	0.6758	0.6285	0.046*
C10	0.96774 (19)	0.8648 (2)	0.73648 (10)	0.0388 (6)
H10A	0.9768	0.8661	0.7805	0.047*
H10B	1.0534	0.8785	0.7267	0.047*
C11	0.56314 (16)	0.79885 (16)	0.71860 (8)	0.0231 (4)
C12	0.38254 (16)	0.71301 (17)	0.73315 (8)	0.0261 (4)
C13	0.34350 (17)	0.84426 (19)	0.81387 (9)	0.0301 (5)
H13A	0.3250	0.9247	0.8083	0.036*
H13B	0.2601	0.8051	0.8095	0.036*
C14	0.52571 (18)	0.90045 (18)	0.89159 (9)	0.0335 (5)
H14A	0.4996	0.9786	0.8827	0.040*
H14B	0.5932	0.8815	0.8687	0.040*
C15	0.5775 (2)	0.88674 (19)	0.95780 (10)	0.0386 (5)
H15A	0.6520	0.9369	0.9703	0.046*
H15B	0.5103	0.9075	0.9805	0.046*
C16	0.50592 (17)	0.6981 (2)	0.95405 (9)	0.0339 (5)
H16A	0.4395	0.7170	0.9775	0.041*
H16B	0.5323	0.6199	0.9628	0.041*
C17	0.45078 (17)	0.71111 (18)	0.88788 (9)	0.0298 (5)
H17A	0.5154	0.6875	0.8644	0.036*
H17B	0.3742	0.6628	0.8766	0.036*
C18	0.6755 (2)	0.7621 (2)	1.03506 (9)	0.0417 (6)
H18A	0.6078	0.7740	1.0588	0.050*
H18B	0.7399	0.8220	1.0455	0.050*
C19	0.74004 (17)	0.65195 (19)	1.05285 (9)	0.0310 (5)
C20	0.75362 (17)	0.6155 (2)	1.11188 (9)	0.0344 (5)
H20	0.7175	0.6578	1.1397	0.041*
C21	0.81892 (19)	0.5186 (2)	1.13025 (9)	0.0405 (6)
H21	0.8286	0.4956	1.1708	0.049*
C22	0.87039 (19)	0.4547 (2)	1.09039 (10)	0.0410 (6)
H22	0.9145	0.3875	1.1031	0.049*
C23	0.85679 (18)	0.4899 (2)	1.03140 (10)	0.0382 (5)
H23	0.8914	0.4465	1.0035	0.046*
C24	0.79293 (18)	0.5884 (2)	1.01311 (9)	0.0347 (5)
H24	0.7854	0.6125	0.9729	0.042*
C25	0.41941 (16)	0.57102 (17)	0.63287 (8)	0.0248 (4)
H25	0.3335	0.5914	0.6343	0.030*
C26	0.44301 (16)	0.48029 (17)	0.59477 (8)	0.0240 (4)
C27	0.33739 (17)	0.42259 (18)	0.56174 (8)	0.0283 (5)
H27	0.2529	0.4435	0.5654	0.034*	0.762 (3)
C28	0.35374 (19)	0.3367 (2)	0.52428 (9)	0.0359 (5)
H28	0.2811	0.3001	0.5013	0.043*
C29	0.47679 (19)	0.3037 (2)	0.52021 (9)	0.0370 (5)
H29	0.4883	0.2441	0.4944	0.044*
C30	0.58288 (19)	0.35642 (19)	0.55309 (9)	0.0341 (5)
H30	0.6669	0.3317	0.5508	0.041*
C31	0.56677 (17)	0.44516 (18)	0.58934 (8)	0.0276 (4)
H31	0.6401	0.4829	0.6109	0.033*	0.238 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0313 (3)	0.0351 (3)	0.0467 (3)	−0.0086 (2)	0.0159 (2)	−0.0070 (3)
O1	0.0223 (9)	0.0354 (13)	0.0382 (11)	−0.0003 (8)	−0.0007 (7)	−0.0151 (10)
O1'	0.022 (3)	0.035 (4)	0.039 (4)	−0.011 (3)	0.001 (2)	0.004 (3)
N1	0.0281 (8)	0.0193 (9)	0.0243 (8)	0.0006 (7)	0.0045 (6)	−0.0031 (7)
N2	0.0220 (7)	0.0188 (9)	0.0253 (8)	0.0006 (6)	0.0035 (6)	−0.0023 (7)
N3	0.0268 (8)	0.0241 (10)	0.0272 (8)	0.0007 (7)	0.0049 (6)	−0.0011 (8)
N4	0.0265 (8)	0.0235 (10)	0.0303 (9)	0.0012 (7)	0.0077 (6)	−0.0013 (8)
N5	0.0276 (8)	0.0261 (10)	0.0319 (9)	0.0049 (7)	0.0098 (6)	−0.0022 (8)
N6	0.0379 (9)	0.0291 (11)	0.0245 (8)	0.0028 (8)	0.0045 (6)	−0.0043 (8)
C1	0.0238 (9)	0.0221 (11)	0.0226 (9)	−0.0035 (8)	0.0043 (7)	−0.0013 (8)
C2	0.0367 (10)	0.0246 (11)	0.0257 (10)	−0.0061 (9)	0.0060 (8)	−0.0048 (9)
C3	0.0399 (11)	0.0299 (13)	0.0362 (12)	−0.0135 (9)	0.0090 (8)	−0.0107 (10)
C4	0.0456 (12)	0.0371 (14)	0.0355 (12)	−0.0161 (10)	0.0141 (9)	−0.0040 (11)
C5	0.0422 (11)	0.0376 (14)	0.0274 (11)	−0.0156 (10)	0.0133 (8)	−0.0103 (10)
C6	0.0323 (10)	0.0268 (12)	0.0236 (10)	−0.0056 (8)	0.0038 (7)	−0.0013 (9)
C7	0.0250 (9)	0.0281 (12)	0.0294 (10)	−0.0006 (8)	0.0006 (7)	0.0009 (9)
C8	0.0239 (10)	0.0380 (14)	0.0457 (13)	−0.0016 (9)	0.0028 (8)	−0.0058 (11)
C9	0.0290 (10)	0.0391 (14)	0.0495 (13)	−0.0104 (9)	0.0166 (9)	−0.0165 (12)
C10	0.0299 (10)	0.0471 (16)	0.0383 (12)	−0.0105 (10)	0.0041 (8)	−0.0063 (12)
C11	0.0257 (9)	0.0207 (11)	0.0214 (9)	0.0021 (8)	0.0008 (7)	0.0022 (8)
C12	0.0242 (9)	0.0266 (12)	0.0274 (10)	0.0033 (8)	0.0052 (7)	0.0021 (9)
C13	0.0282 (10)	0.0295 (12)	0.0340 (11)	0.0085 (9)	0.0094 (8)	−0.0026 (10)
C14	0.0407 (11)	0.0219 (12)	0.0376 (12)	0.0025 (9)	0.0068 (8)	−0.0055 (10)
C15	0.0472 (12)	0.0302 (13)	0.0372 (12)	0.0036 (10)	0.0055 (9)	−0.0079 (11)
C16	0.0319 (10)	0.0371 (14)	0.0354 (11)	0.0039 (9)	0.0134 (8)	0.0050 (11)
C17	0.0265 (9)	0.0278 (12)	0.0356 (11)	−0.0005 (8)	0.0074 (8)	−0.0021 (10)
C18	0.0562 (13)	0.0440 (16)	0.0245 (11)	0.0063 (11)	0.0072 (9)	−0.0062 (11)
C19	0.0303 (10)	0.0360 (13)	0.0270 (10)	−0.0021 (9)	0.0061 (7)	−0.0032 (10)
C20	0.0299 (10)	0.0482 (15)	0.0255 (10)	−0.0077 (10)	0.0064 (8)	−0.0057 (11)
C21	0.0436 (12)	0.0486 (16)	0.0270 (11)	−0.0115 (11)	0.0015 (9)	0.0031 (11)
C22	0.0397 (12)	0.0388 (15)	0.0405 (13)	−0.0021 (10)	−0.0019 (9)	0.0027 (12)
C23	0.0368 (11)	0.0407 (15)	0.0376 (12)	−0.0005 (10)	0.0088 (9)	−0.0040 (11)
C24	0.0377 (11)	0.0416 (14)	0.0262 (10)	−0.0008 (10)	0.0097 (8)	−0.0006 (10)
C25	0.0248 (9)	0.0248 (11)	0.0235 (9)	−0.0002 (8)	0.0020 (7)	0.0033 (9)
C26	0.0292 (9)	0.0205 (11)	0.0217 (9)	−0.0020 (8)	0.0037 (7)	0.0014 (8)
C27	0.0283 (10)	0.0304 (12)	0.0254 (10)	−0.0076 (8)	0.0035 (7)	0.0021 (9)
C28	0.0397 (11)	0.0362 (13)	0.0307 (11)	−0.0144 (10)	0.0041 (8)	−0.0065 (11)
C29	0.0477 (12)	0.0324 (13)	0.0322 (11)	−0.0070 (10)	0.0107 (9)	−0.0106 (11)
C30	0.0372 (11)	0.0314 (13)	0.0344 (11)	−0.0005 (9)	0.0090 (8)	−0.0060 (10)
C31	0.0300 (10)	0.0258 (11)	0.0259 (10)	−0.0032 (8)	0.0026 (7)	−0.0008 (9)

Geometric parameters (Å, º) top

S1—C12	1.670 (2)	C9—H9A	0.9900
O1—C31	1.338 (2)	C9—H9B	0.9900
O1—H1o	0.8400	C10—H10A	0.9900
O1'—C27	1.259 (6)	C10—H10B	0.9900
O1'—H1o'	0.8400	C13—H13A	0.9900
N1—C25	1.285 (2)	C13—H13B	0.9900
N1—N2	1.402 (2)	C14—C15	1.511 (3)
N2—C11	1.384 (2)	C14—H14A	0.9900
N2—C12	1.391 (2)	C14—H14B	0.9900
N3—C11	1.301 (2)	C15—H15A	0.9900
N3—N4	1.384 (2)	C15—H15B	0.9900
N4—C12	1.345 (3)	C16—C17	1.515 (3)
N4—C13	1.477 (2)	C16—H16A	0.9900
N5—C13	1.442 (2)	C16—H16B	0.9900
N5—C17	1.462 (3)	C17—H17A	0.9900
N5—C14	1.466 (3)	C17—H17B	0.9900
N6—C18	1.465 (3)	C18—C19	1.509 (3)
N6—C15	1.465 (3)	C18—H18A	0.9900
N6—C16	1.467 (3)	C18—H18B	0.9900
C1—C11	1.507 (2)	C19—C24	1.384 (3)
C1—C6	1.541 (3)	C19—C20	1.395 (3)
C1—C2	1.542 (3)	C20—C21	1.378 (3)
C1—C7	1.548 (3)	C20—H20	0.9500
C2—C3	1.540 (3)	C21—C22	1.381 (3)
C2—H2A	0.9900	C21—H21	0.9500
C2—H2B	0.9900	C22—C23	1.390 (3)
C3—C10	1.529 (3)	C22—H22	0.9500
C3—C4	1.532 (3)	C23—C24	1.387 (3)
C3—H3	1.0000	C23—H23	0.9500
C4—C5	1.530 (3)	C24—H24	0.9500
C4—H4A	0.9900	C25—C26	1.446 (3)
C4—H4B	0.9900	C25—H25	0.9500
C5—C9	1.527 (3)	C26—C27	1.405 (3)
C5—C6	1.536 (2)	C26—C31	1.407 (2)
C5—H5	1.0000	C27—C28	1.373 (3)
C6—H6A	0.9900	C27—H27	0.9500
C6—H6B	0.9900	C28—C29	1.384 (3)
C7—C8	1.530 (3)	C28—H28	0.9500
C7—H7A	0.9900	C29—C30	1.378 (3)
C7—H7B	0.9900	C29—H29	0.9500
C8—C10	1.533 (3)	C30—C31	1.381 (3)
C8—C9	1.532 (3)	C30—H30	0.9500
C8—H8	1.0000	C31—H31	0.9500

C31—O1—H1o	109.5	N2—C12—S1	130.17 (15)
C27—O1'—H1o'	109.5	N5—C13—N4	114.97 (15)
C25—N1—N2	116.93 (15)	N5—C13—H13A	108.5
C11—N2—C12	108.71 (15)	N4—C13—H13A	108.5
C11—N2—N1	121.94 (14)	N5—C13—H13B	108.5
C12—N2—N1	128.61 (15)	N4—C13—H13B	108.5
C11—N3—N4	104.76 (15)	H13A—C13—H13B	107.5
C12—N4—N3	113.70 (14)	N5—C14—C15	109.01 (18)
C12—N4—C13	126.25 (16)	N5—C14—H14A	109.9
N3—N4—C13	119.47 (16)	C15—C14—H14A	109.9
C13—N5—C17	114.32 (17)	N5—C14—H14B	109.9
C13—N5—C14	114.64 (17)	C15—C14—H14B	109.9
C17—N5—C14	110.63 (15)	H14A—C14—H14B	108.3
C18—N6—C15	109.38 (17)	N6—C15—C14	110.42 (18)
C18—N6—C16	112.46 (17)	N6—C15—H15A	109.6
C15—N6—C16	109.15 (16)	C14—C15—H15A	109.6
C11—C1—C6	112.95 (14)	N6—C15—H15B	109.6
C11—C1—C2	108.80 (15)	C14—C15—H15B	109.6
C6—C1—C2	108.42 (16)	H15A—C15—H15B	108.1
C11—C1—C7	108.15 (15)	N6—C16—C17	109.94 (17)
C6—C1—C7	110.25 (16)	N6—C16—H16A	109.7
C2—C1—C7	108.17 (15)	C17—C16—H16A	109.7
C3—C2—C1	109.95 (16)	N6—C16—H16B	109.7
C3—C2—H2A	109.7	C17—C16—H16B	109.7
C1—C2—H2A	109.7	H16A—C16—H16B	108.2
C3—C2—H2B	109.7	N5—C17—C16	110.46 (18)
C1—C2—H2B	109.7	N5—C17—H17A	109.6
H2A—C2—H2B	108.2	C16—C17—H17A	109.6
C10—C3—C4	109.31 (18)	N5—C17—H17B	109.6
C10—C3—C2	109.67 (18)	C16—C17—H17B	109.6
C4—C3—C2	109.30 (16)	H17A—C17—H17B	108.1
C10—C3—H3	109.5	N6—C18—C19	114.52 (18)
C4—C3—H3	109.5	N6—C18—H18A	108.6
C2—C3—H3	109.5	C19—C18—H18A	108.6
C5—C4—C3	109.49 (18)	N6—C18—H18B	108.6
C5—C4—H4A	109.8	C19—C18—H18B	108.6
C3—C4—H4A	109.8	H18A—C18—H18B	107.6
C5—C4—H4B	109.8	C24—C19—C20	118.6 (2)
C3—C4—H4B	109.8	C24—C19—C18	121.94 (19)
H4A—C4—H4B	108.2	C20—C19—C18	119.41 (19)
C9—C5—C4	109.74 (17)	C21—C20—C19	120.7 (2)
C9—C5—C6	109.24 (17)	C21—C20—H20	119.7
C4—C5—C6	109.68 (17)	C19—C20—H20	119.7
C9—C5—H5	109.4	C20—C21—C22	120.7 (2)
C4—C5—H5	109.4	C20—C21—H21	119.6
C6—C5—H5	109.4	C22—C21—H21	119.6
C5—C6—C1	109.46 (15)	C21—C22—C23	119.1 (2)
C5—C6—H6A	109.8	C21—C22—H22	120.5
C1—C6—H6A	109.8	C23—C22—H22	120.5
C5—C6—H6B	109.8	C24—C23—C22	120.2 (2)
C1—C6—H6B	109.8	C24—C23—H23	119.9
H6A—C6—H6B	108.2	C22—C23—H23	119.9
C8—C7—C1	110.02 (17)	C19—C24—C23	120.7 (2)
C8—C7—H7A	109.7	C19—C24—H24	119.6
C1—C7—H7A	109.7	C23—C24—H24	119.6
C8—C7—H7B	109.7	N1—C25—C26	120.69 (16)
C1—C7—H7B	109.7	N1—C25—H25	119.7
H7A—C7—H7B	108.2	C26—C25—H25	119.7
C7—C8—C10	109.03 (17)	C27—C26—C31	117.66 (18)
C7—C8—C9	109.07 (15)	C27—C26—C25	118.77 (16)
C10—C8—C9	109.61 (19)	C31—C26—C25	123.56 (16)
C7—C8—H8	109.7	O1'—C27—C28	122.6 (3)
C10—C8—H8	109.7	O1'—C27—C26	115.9 (3)
C9—C8—H8	109.7	C28—C27—C26	121.40 (18)
C5—C9—C8	110.21 (18)	C28—C27—H27	119.3
C5—C9—H9A	109.6	C26—C27—H27	119.3
C8—C9—H9A	109.6	C27—C28—C29	119.47 (18)
C5—C9—H9B	109.6	C27—C28—H28	120.3
C8—C9—H9B	109.6	C29—C28—H28	120.3
H9A—C9—H9B	108.1	C30—C29—C28	120.8 (2)
C3—C10—C8	109.80 (16)	C30—C29—H29	119.6
C3—C10—H10A	109.7	C28—C29—H29	119.6
C8—C10—H10A	109.7	C31—C30—C29	119.85 (19)
C3—C10—H10B	109.7	C31—C30—H30	120.1
C8—C10—H10B	109.7	C29—C30—H30	120.1
H10A—C10—H10B	108.2	O1—C31—C30	118.39 (18)
N3—C11—N2	110.28 (16)	O1—C31—C26	120.87 (19)
N3—C11—C1	123.49 (17)	C30—C31—C26	120.74 (17)
N2—C11—C1	126.09 (17)	C30—C31—H31	119.6
N4—C12—N2	102.50 (15)	C26—C31—H31	119.6
N4—C12—S1	127.33 (14)

C25—N1—N2—C11	−153.92 (17)	C11—N2—C12—N4	1.88 (19)
C25—N1—N2—C12	37.0 (3)	N1—N2—C12—N4	172.08 (16)
C11—N3—N4—C12	−0.5 (2)	C11—N2—C12—S1	−177.78 (15)
C11—N3—N4—C13	171.33 (16)	N1—N2—C12—S1	−7.6 (3)
C11—C1—C2—C3	176.65 (15)	C17—N5—C13—N4	−57.1 (2)
C6—C1—C2—C3	−60.2 (2)	C14—N5—C13—N4	72.1 (2)
C7—C1—C2—C3	59.4 (2)	C12—N4—C13—N5	103.4 (2)
C1—C2—C3—C10	−59.7 (2)	N3—N4—C13—N5	−67.3 (2)
C1—C2—C3—C4	60.1 (2)	C13—N5—C14—C15	170.69 (16)
C10—C3—C4—C5	60.4 (2)	C17—N5—C14—C15	−58.3 (2)
C2—C3—C4—C5	−59.7 (2)	C18—N6—C15—C14	176.07 (17)
C3—C4—C5—C9	−59.7 (2)	C16—N6—C15—C14	−60.5 (2)
C3—C4—C5—C6	60.3 (2)	N5—C14—C15—N6	60.0 (2)
C9—C5—C6—C1	59.5 (2)	C18—N6—C16—C17	−179.65 (17)
C4—C5—C6—C1	−60.8 (2)	C15—N6—C16—C17	58.8 (2)
C11—C1—C6—C5	−179.12 (17)	C13—N5—C17—C16	−171.07 (15)
C2—C1—C6—C5	60.2 (2)	C14—N5—C17—C16	57.7 (2)
C7—C1—C6—C5	−58.0 (2)	N6—C16—C17—N5	−57.8 (2)
C11—C1—C7—C8	−178.13 (16)	C15—N6—C18—C19	−170.56 (18)
C6—C1—C7—C8	57.9 (2)	C16—N6—C18—C19	68.0 (2)
C2—C1—C7—C8	−60.5 (2)	N6—C18—C19—C24	28.6 (3)
C1—C7—C8—C10	61.0 (2)	N6—C18—C19—C20	−155.13 (18)
C1—C7—C8—C9	−58.6 (2)	C24—C19—C20—C21	0.4 (3)
C4—C5—C9—C8	58.9 (2)	C18—C19—C20—C21	−176.06 (19)
C6—C5—C9—C8	−61.4 (2)	C19—C20—C21—C22	−1.1 (3)
C7—C8—C9—C5	60.9 (2)	C20—C21—C22—C23	0.7 (3)
C10—C8—C9—C5	−58.4 (2)	C21—C22—C23—C24	0.3 (3)
C4—C3—C10—C8	−60.2 (2)	C20—C19—C24—C23	0.7 (3)
C2—C3—C10—C8	59.6 (2)	C18—C19—C24—C23	177.0 (2)
C7—C8—C10—C3	−60.3 (2)	C22—C23—C24—C19	−1.1 (3)
C9—C8—C10—C3	59.1 (2)	N2—N1—C25—C26	−178.69 (16)
N4—N3—C11—N2	1.70 (19)	N1—C25—C26—C27	178.57 (18)
N4—N3—C11—C1	−174.38 (16)	N1—C25—C26—C31	−0.6 (3)
C12—N2—C11—N3	−2.4 (2)	C31—C26—C27—O1'	−179.0 (3)
N1—N2—C11—N3	−173.33 (15)	C25—C26—C27—O1'	1.8 (4)
C12—N2—C11—C1	173.59 (17)	C31—C26—C27—C28	−1.6 (3)
N1—N2—C11—C1	2.6 (3)	C25—C26—C27—C28	179.19 (19)
C6—C1—C11—N3	−130.8 (2)	O1'—C27—C28—C29	179.2 (4)
C2—C1—C11—N3	−10.4 (2)	C26—C27—C28—C29	2.0 (3)
C7—C1—C11—N3	106.9 (2)	C27—C28—C29—C30	−0.3 (3)
C6—C1—C11—N2	53.8 (3)	C28—C29—C30—C31	−1.8 (3)
C2—C1—C11—N2	174.19 (17)	C29—C30—C31—O1	−177.4 (2)
C7—C1—C11—N2	−68.5 (2)	C29—C30—C31—C26	2.2 (3)
N3—N4—C12—N2	−0.9 (2)	C27—C26—C31—O1	179.11 (19)
C13—N4—C12—N2	−172.05 (16)	C25—C26—C31—O1	−1.7 (3)
N3—N4—C12—S1	178.77 (14)	C27—C26—C31—C30	−0.5 (3)
C13—N4—C12—S1	7.6 (3)	C25—C26—C31—C30	178.67 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.84	1.89	2.632 (2)	147
O1′—H1o′···N5ⁱ	0.84	1.92	2.714 (6)	158
C13—H13A···S1ⁱⁱ	0.99	2.68	3.650 (2)	166
C30—H30···N6ⁱⁱⁱ	0.95	2.54	3.484 (3)	172

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

Experimental details

Crystal data
Chemical formula	C₃₁H₃₈N₆OS
M_r	542.73
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.6015 (5), 12.0283 (7), 22.7865 (12)
β (°)	101.222 (4)
V (Å³)	2850.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.40 × 0.40 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.570, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11447, 6530, 4526
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.125, 1.02
No. of reflections	6530
No. of parameters	364
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.29

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···N1	0.84	1.89	2.632 (2)	147
O1'—H1o'···N5ⁱ	0.84	1.92	2.714 (6)	158
C13—H13A···S1ⁱⁱ	0.99	2.68	3.650 (2)	166
C30—H30···N6ⁱⁱⁱ	0.95	2.54	3.484 (3)	172

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

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. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (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
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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Volume 68| Part 6| June 2012| Pages o1766-o1767

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