Literature DB >> 22412559

3-(Adamantan-1-yl)-4-(prop-2-en-1-yl)-1H-1,2,4-triazole-5(4H)-thione.

Maha S Almutairi, Mona M Al-Shehri, Ali A El-Emam, Seik Weng Ng, Edward R T Tiekink.

Abstract

The title mol-ecule, C(15)H(21)N(3)S, exists as the thione tautomer in the solid state. The 1,2,4-triazole ring is almost planar (r.m.s. deviation = 0.004 Å) and the prop-2-en-1-yl chain is close to being perpendicular to this plane [C-N-C-C torsion angle = 77.1 (5)°]. In the crystal, centrosymmetric dimeric aggregates are formed by pairs of N-H⋯S hydrogen bonds as parts of eight-membered (⋯HNCS)(2) synthons. These are connected into layers parallel to (101) via C-H⋯π inter-actions, where the π-system is the triazole ring. The investigated sample was a nonmerohedral twin; the refined domain ratio was 0.655 (4):0.345 (4).

Entities: Chemical Disease Gene

Year: 2012 PMID： 22412559 PMCID： PMC3295448 DOI： 10.1107/S1600536812005065

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the biological activity of adamantyl derivatives, see: Vernier et al. (1969 ▶); El-Emam et al. (2004 ▶). Kadi et al. (2007 ▶, 2010 ▶). For the biological activity of adamantyl-1,2,4-triazole derivatives, see: Al-Deeb et al. (2006 ▶). For the separation of diffraction data into twin domains, see: Spek (2009 ▶).

Experimental

Crystal data

C15H21N3S M = 275.41 Monoclinic, a = 13.5833 (17) Å b = 8.6483 (6) Å c = 13.6973 (14) Å β = 115.938 (14)° V = 1447.0 (3) Å3 Z = 4 Mo Kα radiation μ = 0.22 mm−1 T = 100 K 0.35 × 0.15 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.929, T max = 0.979 10998 measured reflections 3324 independent reflections 2875 reflections with I > 2σ(I) R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.081 wR(F 2) = 0.230 S = 1.17 3324 reflections 173 parameters H-atom parameters constrained Δρmax = 0.71 e Å−3 Δρmin = −0.66 e Å−3 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 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005065/hb6626sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005065/hb6626Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812005065/hb6626Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₂₁N₃S	F(000) = 592
M_r = 275.41	D_x = 1.264 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1371 reflections
a = 13.5833 (17) Å	θ = 2.4–27.5°
b = 8.6483 (6) Å	µ = 0.22 mm⁻¹
c = 13.6973 (14) Å	T = 100 K
β = 115.938 (14)°	Prism, colourless
V = 1447.0 (3) Å³	0.35 × 0.15 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with Atlas detector	3324 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2875 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.077
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.8°
ω scans	h = −17→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→11
T_min = 0.929, T_max = 0.979	l = −6→17
10998 measured reflections

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.230	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0882P)² + 4.0546P] where P = (F_o² + 2F_c²)/3
3324 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	U_iso*/U_eq
S1	0.60052 (9)	0.72236 (11)	0.51878 (8)	0.0170 (3)
N1	0.6426 (3)	0.7440 (4)	0.7336 (3)	0.0115 (6)
N2	0.5548 (3)	0.5391 (4)	0.6557 (3)	0.0137 (7)
H2N	0.5203	0.4685	0.6062	0.016*
N3	0.5707 (3)	0.5286 (4)	0.7620 (3)	0.0141 (7)
C1	0.5976 (3)	0.6683 (5)	0.6357 (3)	0.0127 (7)
C2	0.6240 (3)	0.6536 (4)	0.8078 (3)	0.0124 (7)
C3	0.6643 (3)	0.6857 (5)	0.9271 (3)	0.0124 (7)
C4	0.7912 (3)	0.6936 (5)	0.9857 (3)	0.0152 (8)
H4A	0.8224	0.5954	0.9747	0.018*
H4B	0.8173	0.7784	0.9544	0.018*
C5	0.8298 (4)	0.7216 (5)	1.1068 (3)	0.0190 (9)
H5	0.9115	0.7286	1.1435	0.023*
C6	0.7923 (4)	0.5877 (6)	1.1559 (3)	0.0238 (10)
H6A	0.8176	0.6052	1.2346	0.029*
H6B	0.8245	0.4895	1.1462	0.029*
C7	0.6670 (4)	0.5770 (6)	1.0993 (3)	0.0222 (9)
H7	0.6429	0.4885	1.1307	0.027*
C8	0.6281 (3)	0.5500 (5)	0.9779 (3)	0.0176 (8)
H8A	0.5473	0.5411	0.9419	0.021*
H8B	0.6592	0.4520	0.9665	0.021*
C9	0.6144 (3)	0.8368 (5)	0.9470 (3)	0.0170 (8)
H9A	0.6361	0.9254	0.9149	0.020*
H9B	0.5335	0.8296	0.9113	0.020*
C10	0.6547 (4)	0.8630 (6)	1.0692 (3)	0.0228 (10)
H10	0.6233	0.9618	1.0813	0.027*
C11	0.7803 (4)	0.8738 (6)	1.1234 (3)	0.0232 (9)
H11A	0.8069	0.8941	1.2020	0.028*
H11B	0.8037	0.9605	1.0914	0.028*
C12	0.6173 (4)	0.7278 (6)	1.1179 (4)	0.0263 (11)
H12A	0.5364	0.7208	1.0826	0.032*
H12B	0.6419	0.7447	1.1966	0.032*
C13	0.6875 (3)	0.9016 (5)	0.7431 (3)	0.0157 (8)
H13A	0.7316	0.9079	0.7017	0.019*
H13B	0.7365	0.9237	0.8202	0.019*
C14	0.5979 (4)	1.0210 (5)	0.7008 (3)	0.0180 (8)
H14	0.5409	1.0080	0.6295	0.022*
C15	0.5939 (4)	1.1433 (5)	0.7573 (4)	0.0234 (10)
H15A	0.6497	1.1593	0.8288	0.035*
H15B	0.5353	1.2149	0.7264	0.035*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0220 (6)	0.0180 (5)	0.0114 (5)	−0.0044 (4)	0.0077 (4)	−0.0016 (4)
N1	0.0121 (15)	0.0121 (14)	0.0112 (15)	−0.0009 (13)	0.0058 (12)	0.0001 (12)
N2	0.0165 (16)	0.0116 (15)	0.0109 (14)	−0.0005 (13)	0.0039 (12)	−0.0013 (12)
N3	0.0173 (16)	0.0125 (16)	0.0114 (15)	0.0001 (13)	0.0051 (12)	−0.0014 (12)
C1	0.0131 (17)	0.0137 (18)	0.0104 (16)	0.0001 (15)	0.0043 (13)	−0.0016 (14)
C2	0.0137 (18)	0.0119 (17)	0.0127 (17)	−0.0005 (14)	0.0067 (14)	0.0010 (14)
C3	0.0135 (18)	0.0150 (18)	0.0108 (16)	−0.0018 (15)	0.0073 (14)	0.0003 (14)
C4	0.0156 (19)	0.0188 (19)	0.0121 (17)	−0.0012 (16)	0.0070 (14)	0.0014 (15)
C5	0.0162 (19)	0.025 (2)	0.0129 (18)	−0.0087 (17)	0.0038 (15)	0.0021 (16)
C6	0.023 (2)	0.031 (2)	0.0132 (18)	−0.0073 (19)	0.0042 (16)	0.0063 (17)
C7	0.023 (2)	0.029 (2)	0.0146 (18)	−0.0090 (19)	0.0088 (16)	0.0029 (17)
C8	0.0174 (19)	0.019 (2)	0.0155 (18)	−0.0065 (16)	0.0063 (15)	0.0016 (15)
C9	0.0181 (19)	0.0167 (19)	0.0173 (19)	−0.0002 (16)	0.0087 (16)	−0.0039 (15)
C10	0.026 (2)	0.030 (2)	0.0175 (19)	−0.0006 (19)	0.0137 (17)	−0.0061 (17)
C11	0.027 (2)	0.029 (2)	0.0150 (18)	−0.0116 (19)	0.0107 (17)	−0.0096 (17)
C12	0.024 (2)	0.043 (3)	0.016 (2)	−0.009 (2)	0.0134 (17)	−0.0073 (19)
C13	0.0161 (19)	0.015 (2)	0.0144 (17)	−0.0059 (15)	0.0054 (15)	−0.0007 (14)
C14	0.021 (2)	0.0132 (18)	0.0178 (18)	−0.0031 (16)	0.0071 (16)	0.0015 (15)
C15	0.030 (2)	0.015 (2)	0.024 (2)	−0.0007 (18)	0.0103 (18)	0.0003 (17)

S1—C1	1.685 (4)	C7—C12	1.539 (7)
N1—C1	1.372 (5)	C7—H7	1.0000
N1—C2	1.390 (5)	C8—H8A	0.9900
N1—C13	1.476 (5)	C8—H8B	0.9900
N2—C1	1.342 (5)	C9—C10	1.534 (6)
N2—N3	1.379 (5)	C9—H9A	0.9900
N2—H2N	0.8800	C9—H9B	0.9900
N3—C2	1.300 (5)	C10—C11	1.537 (6)
C2—C3	1.504 (5)	C10—C12	1.538 (7)
C3—C8	1.550 (5)	C10—H10	1.0000
C3—C9	1.551 (6)	C11—H11A	0.9900
C3—C4	1.552 (5)	C11—H11B	0.9900
C4—C5	1.525 (5)	C12—H12A	0.9900
C4—H4A	0.9900	C12—H12B	0.9900
C4—H4B	0.9900	C13—C14	1.506 (6)
C5—C6	1.533 (6)	C13—H13A	0.9900
C5—C11	1.539 (7)	C13—H13B	0.9900
C5—H5	1.0000	C14—C15	1.326 (6)
C6—C7	1.534 (6)	C14—H14	0.9500
C6—H6A	0.9900	C15—H15A	0.9500
C6—H6B	0.9900	C15—H15B	0.9500
C7—C8	1.527 (6)

C1—N1—C2	107.5 (3)	C7—C8—C3	110.3 (3)
C1—N1—C13	121.1 (3)	C7—C8—H8A	109.6
C2—N1—C13	131.0 (3)	C3—C8—H8A	109.6
C1—N2—N3	112.9 (3)	C7—C8—H8B	109.6
C1—N2—H2N	123.6	C3—C8—H8B	109.6
N3—N2—H2N	123.6	H8A—C8—H8B	108.1
C2—N3—N2	104.6 (3)	C10—C9—C3	110.0 (3)
N2—C1—N1	104.2 (3)	C10—C9—H9A	109.7
N2—C1—S1	128.1 (3)	C3—C9—H9A	109.7
N1—C1—S1	127.7 (3)	C10—C9—H9B	109.7
N3—C2—N1	110.8 (3)	C3—C9—H9B	109.7
N3—C2—C3	122.6 (3)	H9A—C9—H9B	108.2
N1—C2—C3	126.4 (3)	C9—C10—C11	109.1 (3)
C2—C3—C8	108.2 (3)	C9—C10—C12	109.4 (4)
C2—C3—C9	111.5 (3)	C11—C10—C12	110.1 (4)
C8—C3—C9	108.1 (3)	C9—C10—H10	109.4
C2—C3—C4	111.4 (3)	C11—C10—H10	109.4
C8—C3—C4	107.5 (3)	C12—C10—H10	109.4
C9—C3—C4	110.1 (3)	C10—C11—C5	110.0 (4)
C5—C4—C3	110.2 (3)	C10—C11—H11A	109.7
C5—C4—H4A	109.6	C5—C11—H11A	109.7
C3—C4—H4A	109.6	C10—C11—H11B	109.7
C5—C4—H4B	109.6	C5—C11—H11B	109.7
C3—C4—H4B	109.6	H11A—C11—H11B	108.2
H4A—C4—H4B	108.1	C10—C12—C7	108.7 (4)
C4—C5—C6	109.6 (3)	C10—C12—H12A	110.0
C4—C5—C11	109.4 (3)	C7—C12—H12A	110.0
C6—C5—C11	109.3 (4)	C10—C12—H12B	110.0
C4—C5—H5	109.5	C7—C12—H12B	110.0
C6—C5—H5	109.5	H12A—C12—H12B	108.3
C11—C5—H5	109.5	N1—C13—C14	111.4 (3)
C5—C6—C7	109.4 (4)	N1—C13—H13A	109.3
C5—C6—H6A	109.8	C14—C13—H13A	109.3
C7—C6—H6A	109.8	N1—C13—H13B	109.3
C5—C6—H6B	109.8	C14—C13—H13B	109.3
C7—C6—H6B	109.8	H13A—C13—H13B	108.0
H6A—C6—H6B	108.2	C15—C14—C13	123.7 (4)
C8—C7—C6	109.7 (4)	C15—C14—H14	118.2
C8—C7—C12	110.0 (4)	C13—C14—H14	118.2
C6—C7—C12	109.6 (4)	C14—C15—H15A	120.0
C8—C7—H7	109.2	C14—C15—H15B	120.0
C6—C7—H7	109.2	H15A—C15—H15B	120.0
C12—C7—H7	109.2

C1—N2—N3—C2	0.0 (4)	C11—C5—C6—C7	60.0 (5)
N3—N2—C1—N1	−0.1 (4)	C5—C6—C7—C8	59.5 (5)
N3—N2—C1—S1	177.5 (3)	C5—C6—C7—C12	−61.4 (5)
C2—N1—C1—N2	0.2 (4)	C6—C7—C8—C3	−60.4 (5)
C13—N1—C1—N2	−173.0 (3)	C12—C7—C8—C3	60.3 (5)
C2—N1—C1—S1	−177.5 (3)	C2—C3—C8—C7	−179.9 (3)
C13—N1—C1—S1	9.3 (6)	C9—C3—C8—C7	−59.1 (4)
N2—N3—C2—N1	0.1 (4)	C4—C3—C8—C7	59.7 (4)
N2—N3—C2—C3	−176.5 (3)	C2—C3—C9—C10	178.3 (3)
C1—N1—C2—N3	−0.2 (5)	C8—C3—C9—C10	59.6 (4)
C13—N1—C2—N3	172.1 (4)	C4—C3—C9—C10	−57.5 (4)
C1—N1—C2—C3	176.2 (4)	C3—C9—C10—C11	59.2 (5)
C13—N1—C2—C3	−11.5 (7)	C3—C9—C10—C12	−61.3 (5)
N3—C2—C3—C8	−1.5 (5)	C9—C10—C11—C5	−61.2 (5)
N1—C2—C3—C8	−177.5 (4)	C12—C10—C11—C5	58.9 (4)
N3—C2—C3—C9	−120.2 (4)	C4—C5—C11—C10	61.1 (4)
N1—C2—C3—C9	63.8 (5)	C6—C5—C11—C10	−58.9 (4)
N3—C2—C3—C4	116.4 (4)	C9—C10—C12—C7	60.6 (5)
N1—C2—C3—C4	−59.6 (5)	C11—C10—C12—C7	−59.3 (4)
C2—C3—C4—C5	−178.4 (3)	C8—C7—C12—C10	−60.2 (4)
C8—C3—C4—C5	−60.1 (4)	C6—C7—C12—C10	60.6 (4)
C9—C3—C4—C5	57.4 (4)	C1—N1—C13—C14	77.1 (5)
C3—C4—C5—C6	61.0 (5)	C2—N1—C13—C14	−94.3 (5)
C3—C4—C5—C11	−58.8 (4)	N1—C13—C14—C15	126.8 (4)
C4—C5—C6—C7	−59.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···S1ⁱ	0.88	2.43	3.296 (3)	170
C5—H5···Cg1ⁱⁱ	1.00	2.60	3.529 (6)	155
C13—H13A···Cg1ⁱⁱⁱ	0.99	2.81	3.351 (5)	115

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1/C2/N1/N2/N3 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯S1ⁱ	0.88	2.43	3.296 (3)	170
C5—H5⋯Cg1ⁱⁱ	1.00	2.60	3.529 (6)	155
C13—H13A⋯Cg1ⁱⁱⁱ	0.99	2.81	3.351 (5)	115

Symmetry codes: (i) ; (ii) ; (iii) .

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2. The toxicologic and pharmacologic properties of amantadine hydrochloride.

Authors: V G Vernier; J B Harmon; J M Stump; T E Lynes; J P Marvel; D H Smith
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4. Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles.

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5. Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones.

Authors: Ali A El-Emam; Omar A Al-Deeb; Mohamed Al-Omar; Jochen Lehmann
Journal: Bioorg Med Chem Date: 2004-10-01 Impact factor: 3.641

6. Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-[3-(1-adamantyl)-4-substituted-5-thioxo-1,2,4-triazolin-1-yl] acetic acids, 2-[3-(1-adamantyl)-4-substituted-5-thioxo-1,2,4-triazolin-1-yl]propionic acids and related derivatives.

Authors: Omar A Al-Deeb; Mohamed A Al-Omar; Nasser R El-Brollosy; Elsayed E Habib; Tarek M Ibrahim; Ali A El-Emam
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Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20

7 in total

13 in total

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Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-04-13

2. 2-{[5-(Adamantan-1-yl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfan-yl}-N,N-dimethyl-ethanamine.

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Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-04-13

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4. 1-(Adamantan-1-yl)-3-(4-fluoro-phen-yl)thio-urea.

Authors: Güneş Demirtaş; Necmi Dege; Mona M Al-Shehri; Ali A El-Emam; Nasser R El-Brollosy; Orhan Büyükgüngör
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-04-25

5. 5-(Adamantan-1-yl)-3-[(2-meth-oxy-eth-yl)sulfan-yl]-4-phenyl-4H-1,2,4-triazole.

Authors: Ali A El-Emam; Ebtehal S Al-Abdullah; Hanadi H Asiri; Suchada Chantrapromma; Hoong-Kun Fun
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-07-04

6. 5-(Adamantan-1-yl)-N-methyl-1,3,4-thia-diazol-2-amine.

Authors: Abdul-Malek S Al-Tamimi; Ahmed M Alafeefy; Ali A El-Emam; Seik Weng Ng; Edward R T Tiekink
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2013-04-10

7. 3-(Adamantan-1-yl)-4-[(E)-(2,6-di-fluoro-benzyl-idene)amino]-1-[(4-ethyl-piperazin-1-yl)meth-yl]-4,5-di-hydro-1H-1,2,4-triazole-5-thione.

Authors: Abdul-Malek S Al-Tamimi; Ebtehal S Al-Abdullah; Ali A El-Emam; Seik Weng Ng; Edward R T Tiekink
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2013-04-10