3-(Adamantan-1-yl)-4-phenyl-1-[(4-phenyl­piperazin-1-yl)meth­yl]-1H-1,2,4-triazole-5(4H)-thione

Al-Abdullah, E.S.; Asiri, H.H.; El-Emam, A.; Ng, S.W.

doi:10.1107/S1600536811055711

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o345

doi:10.1107/S1600536811055711

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3-(Adamantan-1-yl)-4-phenyl-1-[(4-phenylpiperazin-1-yl)methyl]-1H-1,2,4-triazole-5(4H)-thione

Ebtehal S. Al-Abdullah,^a Hanadi H. Asiri,^a Ali El-Emam ^a and Seik Weng Ng ^b,^c ^*

^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: seikweng@um.edu.my

(Received 19 December 2011; accepted 26 December 2011; online 11 January 2012)

The title molecule, C₂₉H₃₅N₅S, displays a chair-shaped piperazine ring, as well as an approximately planar triazole ring (r.m.s. deviation = 0.001 Å) whose phenyl substituent is nearly perpendicular to the mean plane of the five-membered ring [dihedral angle = 88.9 (1)°]. The substituents on the piperazine ring occupy equatorial sites. In the crystal, the adamantyl cage is disordered over two sets of sites with a major component of 67.8 (5)%. Weak intermolecular C—H⋯S hydrogen bonding is present in the crystal.

Related literature

For the synthesis and applications of 3-(1-adamantyl)-4-substituted-5-mercapto-1,2,4-triazole derivatives, see: El-Emam & Ibrahim (1991 ).

Experimental

Crystal data

C₂₉H₃₅N₅S
M_r = 485.68
Monoclinic, P 2₁
a = 11.3342 (5) Å
b = 8.4744 (3) Å
c = 13.7868 (6) Å
β = 103.864 (4)°
V = 1285.65 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 100 K
0.40 × 0.35 × 0.30 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.941, T_max = 0.956
8952 measured reflections
5539 independent reflections
5155 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.154
S = 1.02
5537 reflections
398 parameters
169 restraints
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.56 e Å⁻³
Absolute structure: Flack (1983 ), 2382 Friedel pairs
Flack parameter: 0.01 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19B⋯S1ⁱ	0.99	2.84	3.593 (4)	133
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z]$ .

Data collection: CrysAlis PRO (Agilent, 2010); 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811055711/xu5420sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055711/xu5420Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055711/xu5420Isup3.cml

checkCIF report

Comment top

We reported the synthesis, anti-inflammatory and analgesic properties of 3-(1-adamantyl)-4-substituted-5-mercapto-1,2,4-triazole derivatives (El-Emam & Ibrahim, 1991). The triazole ring, which possesses a secondary nitrogen site next to a double-bond sulfur, is capable of undergoing a Mannich reaction with an N-substituted piperazine derivative to yield a new class of chemotherapeutic compounds. The C₂₉H₃₅N₅S molecule (Scheme I, Fig. 1) displays a chair-shaped piperazine ring, as well as a planar triazole ring whose phenyl substituent is nearly perpendicular to the mean plane of the five-membered ring (dihedral angle 88.9 (1) °). The substituents on the piperazine ring occupy equatorial sites. The adamantyl cage is disordered.

Related literature top

For the synthesis and applications of 3-(1-adamantyl)-4-substituted-5-mercapto-1,2,4-triazole derivatives, see: El-Emam & Ibrahim (1991).

Experimental top

5-(1-Adamantyl)-4-phenyl-1,2,4-triazole-3-thiol was synthesized according to a reported procedure (El-Emam & Ibrahim, 1991). The compound (2 mmol), 1-phenylpiperazine (2 mmol) and a 37% formaldehyde solution (0.5 ml) in ethanol (8 ml), was heated for 15 minutes. Stirring was continued for 12 h at room temperature. The product was filtered, washed with water, dried, and recrystallized from ethanol to yield 816 mg (80%) of the title compound as colorless crystals, m.p. 598–500 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₉H₃₅N₅S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The minor disorder component is not shown.

3-(Adamantan-1-yl)-4-phenyl-1-[(4-phenylpiperazin-1-yl)methyl]- 1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₂₉H₃₅N₅S	F(000) = 520
M_r = 485.68	D_x = 1.255 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5784 reflections
a = 11.3342 (5) Å	θ = 2.4–27.5°
b = 8.4744 (3) Å	µ = 0.15 mm⁻¹
c = 13.7868 (6) Å	T = 100 K
β = 103.864 (4)°	Wedge, colorless
V = 1285.65 (9) Å³	0.40 × 0.35 × 0.30 mm
Z = 2

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5539 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5155 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.022
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.8°
ω scan	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→11
T_min = 0.941, T_max = 0.956	l = −13→17
8952 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)] = 0.060	H-atom parameters constrained
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.0713P)² + 1.5877P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
5537 reflections	Δρ_max = 0.72 e Å⁻³
398 parameters	Δρ_min = −0.56 e Å⁻³
169 restraints	Absolute structure: Flack (1983), 2382 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (11)

Crystal data top

C₂₉H₃₅N₅S	V = 1285.65 (9) Å³
M_r = 485.68	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.3342 (5) Å	µ = 0.15 mm⁻¹
b = 8.4744 (3) Å	T = 100 K
c = 13.7868 (6) Å	0.40 × 0.35 × 0.30 mm
β = 103.864 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5539 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	5155 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.956	R_int = 0.022
8952 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.154	Δρ_max = 0.72 e Å⁻³
S = 1.02	Δρ_min = −0.56 e Å⁻³
5537 reflections	Absolute structure: Flack (1983), 2382 Friedel pairs
398 parameters	Absolute structure parameter: 0.01 (11)
169 restraints

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.82856 (7)	0.50082 (16)	0.02316 (5)	0.02700 (18)
N1	0.8127 (2)	0.7494 (3)	0.14650 (19)	0.0224 (5)
N2	1.0027 (2)	0.8295 (4)	0.1988 (2)	0.0281 (6)
N3	0.9950 (2)	0.7016 (3)	0.1347 (2)	0.0253 (6)
N4	1.1767 (2)	0.5280 (4)	0.1622 (2)	0.0254 (6)
N5	1.2418 (2)	0.2718 (4)	0.29827 (19)	0.0244 (6)
C1	0.8801 (3)	0.6498 (4)	0.1015 (2)	0.0224 (6)
C2	0.8918 (3)	0.8563 (4)	0.2051 (2)	0.0246 (6)
C3	0.6821 (3)	0.7415 (4)	0.1239 (3)	0.0297 (7)
C4	0.6262 (4)	0.6461 (5)	0.1808 (3)	0.0438 (10)
H4	0.6729	0.5857	0.2345	0.053*
C5	0.4988 (4)	0.6406 (6)	0.1573 (5)	0.0613 (15)
H5	0.4586	0.5758	0.1956	0.074*
C6	0.4320 (4)	0.7274 (6)	0.0803 (5)	0.0637 (15)
H6	0.3458	0.7228	0.0653	0.076*
C7	0.4887 (4)	0.8215 (6)	0.0240 (5)	0.0593 (14)
H7	0.4416	0.8820	−0.0294	0.071*
C8	0.6154 (3)	0.8283 (5)	0.0452 (3)	0.0404 (9)
H8	0.6550	0.8920	0.0059	0.049*
C9	0.8586 (2)	0.9902 (3)	0.2700 (2)	0.0366 (8)
C10	0.7951 (4)	1.1115 (4)	0.1942 (2)	0.0408 (14)	0.678 (5)
H10A	0.8508	1.1462	0.1530	0.049*	0.678 (5)
H10B	0.7228	1.0630	0.1493	0.049*	0.678 (5)
C11	0.7569 (4)	1.2516 (4)	0.2460 (3)	0.0391 (13)	0.678 (5)
H11	0.7171	1.3314	0.1952	0.047*	0.678 (5)
C12	0.8665 (4)	1.3237 (4)	0.3151 (3)	0.0433 (17)	0.678 (5)
H12A	0.9237	1.3619	0.2761	0.052*	0.678 (5)
H12B	0.8416	1.4149	0.3504	0.052*	0.678 (5)
C13	0.9280 (3)	1.2023 (4)	0.3896 (3)	0.0424 (16)	0.678 (5)
H13	1.0006	1.2506	0.4358	0.051*	0.678 (5)
C14	0.9677 (3)	1.0649 (5)	0.3362 (3)	0.0434 (16)	0.678 (5)
H14A	1.0238	1.1016	0.2959	0.052*	0.678 (5)
H14B	1.0112	0.9869	0.3855	0.052*	0.678 (5)
C15	0.6689 (3)	1.1999 (5)	0.3060 (3)	0.0374 (13)	0.678 (5)
H15A	0.5951	1.1551	0.2611	0.045*	0.678 (5)
H15B	0.6446	1.2916	0.3413	0.045*	0.678 (5)
C16	0.7294 (3)	1.0775 (4)	0.3804 (3)	0.0303 (12)	0.678 (5)
H16	0.6715	1.0419	0.4204	0.036*	0.678 (5)
C17	0.8409 (4)	1.1462 (5)	0.4491 (2)	0.0377 (13)	0.678 (5)
H17A	0.8175	1.2357	0.4867	0.045*	0.678 (5)
H17B	0.8807	1.0652	0.4977	0.045*	0.678 (5)
C18	0.7658 (3)	0.9387 (3)	0.3261 (3)	0.0261 (11)	0.678 (5)
H18A	0.6934	0.8951	0.2786	0.031*	0.678 (5)
H18B	0.8007	0.8549	0.3745	0.031*	0.678 (5)
C19	1.1068 (3)	0.6541 (5)	0.1049 (3)	0.0280 (7)
H19A	1.0839	0.6214	0.0339	0.034*
H19B	1.1599	0.7478	0.1095	0.034*
C20	1.2026 (3)	0.5548 (4)	0.2700 (2)	0.0264 (7)
H20A	1.1261	0.5502	0.2926	0.032*
H20B	1.2384	0.6610	0.2858	0.032*
C21	1.2901 (3)	0.4310 (4)	0.3246 (3)	0.0271 (7)
H21A	1.3693	0.4423	0.3067	0.033*
H21B	1.3037	0.4469	0.3976	0.033*
C22	1.2169 (3)	0.2464 (4)	0.1899 (2)	0.0283 (7)
H22A	1.1828	0.1395	0.1733	0.034*
H22B	1.2933	0.2546	0.1674	0.034*
C23	1.1266 (3)	0.3703 (4)	0.1372 (2)	0.0241 (6)
H23A	1.1094	0.3543	0.0640	0.029*
H23B	1.0493	0.3595	0.1580	0.029*
C24	1.3055 (3)	0.1486 (4)	0.3583 (2)	0.0220 (6)
C25	1.3170 (3)	0.1532 (4)	0.4616 (2)	0.0295 (7)
H25	1.2840	0.2397	0.4902	0.035*
C26	1.3757 (3)	0.0341 (5)	0.5226 (2)	0.0327 (8)
H26	1.3825	0.0393	0.5925	0.039*
C27	1.4254 (3)	−0.0945 (4)	0.4823 (3)	0.0314 (7)
H27	1.4663	−0.1761	0.5244	0.038*
C28	1.4139 (3)	−0.1007 (5)	0.3811 (3)	0.0313 (7)
H28	1.4466	−0.1881	0.3531	0.038*
C29	1.3552 (3)	0.0193 (4)	0.3184 (2)	0.0267 (6)
H29	1.3488	0.0134	0.2485	0.032*
C10'	0.9726 (4)	1.0898 (7)	0.2942 (5)	0.041 (3)	0.322 (5)
H10C	1.0445	1.0199	0.3129	0.050*	0.322 (5)
H10D	0.9787	1.1499	0.2340	0.050*	0.322 (5)
C11'	0.9728 (5)	1.2025 (6)	0.3780 (4)	0.037 (3)	0.322 (5)
H11B	1.0480	1.2687	0.3899	0.045*	0.322 (5)
C12'	0.9704 (5)	1.1144 (8)	0.4720 (4)	0.041 (3)	0.322 (5)
H12C	0.9674	1.1897	0.5263	0.049*	0.322 (5)
H12D	1.0445	1.0492	0.4933	0.049*	0.322 (5)
C13'	0.8595 (5)	1.0112 (6)	0.4507 (3)	0.030 (2)	0.322 (5)
H13'	0.8571	0.9485	0.5116	0.036*	0.322 (5)
C14'	0.8619 (6)	0.9014 (5)	0.3658 (3)	0.034 (3)	0.322 (5)
H14C	0.7912	0.8294	0.3553	0.041*	0.322 (5)
H14D	0.9366	0.8364	0.3832	0.041*	0.322 (5)
C15'	0.8633 (6)	1.3077 (5)	0.3507 (6)	0.037 (4)	0.322 (5)
H15C	0.8626	1.3817	0.4061	0.045*	0.322 (5)
H15D	0.8657	1.3702	0.2905	0.045*	0.322 (5)
C16'	0.7514 (5)	1.2067 (5)	0.3305 (4)	0.027 (2)	0.322 (5)
H16'	0.6780	1.2760	0.3129	0.032*	0.322 (5)
C17'	0.7481 (5)	1.1129 (8)	0.4221 (4)	0.021 (2)	0.322 (5)
H17C	0.6744	1.0459	0.4088	0.025*	0.322 (5)
H17D	0.7448	1.1853	0.4778	0.025*	0.322 (5)
C18'	0.7507 (4)	1.0967 (6)	0.2452 (4)	0.029 (2)	0.322 (5)
H18C	0.6754	1.0329	0.2312	0.035*	0.322 (5)
H18D	0.7521	1.1585	0.1846	0.035*	0.322 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0281 (4)	0.0282 (4)	0.0246 (3)	−0.0012 (3)	0.0061 (3)	0.0004 (3)
N1	0.0228 (12)	0.0208 (13)	0.0263 (13)	0.0058 (10)	0.0115 (10)	0.0054 (10)
N2	0.0273 (13)	0.0260 (14)	0.0299 (14)	0.0066 (11)	0.0044 (11)	−0.0023 (11)
N3	0.0204 (12)	0.0262 (14)	0.0293 (14)	0.0050 (11)	0.0062 (10)	−0.0020 (11)
N4	0.0222 (12)	0.0271 (15)	0.0279 (13)	0.0022 (11)	0.0077 (10)	0.0019 (11)
N5	0.0290 (13)	0.0241 (13)	0.0196 (12)	0.0017 (11)	0.0050 (10)	−0.0029 (10)
C1	0.0254 (14)	0.0236 (15)	0.0195 (13)	0.0044 (12)	0.0080 (11)	0.0064 (12)
C2	0.0282 (15)	0.0243 (16)	0.0229 (14)	0.0048 (13)	0.0092 (12)	0.0059 (12)
C3	0.0234 (15)	0.0252 (17)	0.0460 (19)	0.0028 (13)	0.0191 (14)	0.0057 (14)
C4	0.043 (2)	0.038 (2)	0.062 (3)	0.0016 (18)	0.0353 (19)	0.0087 (19)
C5	0.050 (3)	0.042 (3)	0.112 (4)	−0.014 (2)	0.061 (3)	−0.008 (3)
C6	0.0262 (19)	0.044 (3)	0.130 (5)	0.0000 (19)	0.035 (3)	−0.008 (3)
C7	0.0249 (18)	0.040 (2)	0.109 (4)	0.0076 (18)	0.008 (2)	0.011 (3)
C8	0.0251 (17)	0.034 (2)	0.063 (3)	0.0058 (15)	0.0117 (16)	0.0174 (18)
C9	0.055 (2)	0.0231 (16)	0.0432 (18)	−0.0005 (17)	0.0344 (17)	0.0007 (16)
C10	0.052 (3)	0.025 (3)	0.050 (3)	0.007 (2)	0.023 (3)	−0.004 (2)
C11	0.060 (3)	0.024 (3)	0.038 (3)	0.007 (2)	0.023 (3)	0.001 (2)
C12	0.063 (4)	0.016 (3)	0.062 (4)	−0.006 (3)	0.038 (3)	−0.004 (3)
C13	0.050 (4)	0.038 (3)	0.048 (3)	0.006 (3)	0.029 (3)	−0.017 (3)
C14	0.040 (3)	0.054 (4)	0.030 (3)	0.011 (3)	−0.004 (2)	−0.019 (3)
C15	0.041 (3)	0.033 (3)	0.041 (3)	0.011 (2)	0.016 (2)	−0.008 (2)
C16	0.033 (3)	0.035 (3)	0.026 (3)	−0.002 (2)	0.014 (2)	−0.004 (2)
C17	0.046 (3)	0.036 (3)	0.033 (3)	−0.003 (3)	0.012 (2)	−0.002 (2)
C18	0.030 (2)	0.026 (2)	0.026 (2)	0.0007 (19)	0.0130 (19)	0.0026 (17)
C19	0.0216 (14)	0.0293 (17)	0.0351 (17)	0.0068 (13)	0.0109 (13)	0.0053 (14)
C20	0.0272 (15)	0.0232 (15)	0.0280 (16)	−0.0008 (12)	0.0052 (12)	−0.0068 (12)
C21	0.0256 (15)	0.0261 (16)	0.0279 (16)	−0.0018 (13)	0.0029 (12)	−0.0019 (12)
C22	0.0374 (17)	0.0249 (16)	0.0215 (15)	0.0071 (14)	0.0050 (13)	−0.0010 (12)
C23	0.0283 (15)	0.0235 (16)	0.0194 (14)	0.0037 (13)	0.0035 (11)	−0.0025 (12)
C24	0.0175 (13)	0.0237 (15)	0.0236 (14)	−0.0036 (12)	0.0028 (11)	−0.0018 (12)
C25	0.0301 (16)	0.0308 (17)	0.0278 (16)	0.0007 (14)	0.0071 (13)	−0.0021 (13)
C26	0.0306 (16)	0.042 (2)	0.0238 (15)	−0.0086 (15)	0.0025 (12)	0.0020 (13)
C27	0.0246 (15)	0.0306 (18)	0.0369 (18)	−0.0032 (14)	0.0036 (13)	0.0109 (14)
C28	0.0275 (16)	0.0262 (17)	0.0398 (19)	0.0012 (14)	0.0075 (14)	0.0020 (14)
C29	0.0238 (14)	0.0274 (17)	0.0294 (15)	−0.0007 (14)	0.0074 (11)	−0.0002 (13)
C10'	0.052 (5)	0.041 (5)	0.031 (5)	0.018 (4)	0.009 (4)	−0.019 (4)
C11'	0.042 (5)	0.040 (5)	0.036 (5)	0.017 (4)	0.020 (4)	0.005 (4)
C12'	0.040 (5)	0.039 (5)	0.047 (5)	0.004 (4)	0.016 (4)	0.007 (4)
C13'	0.030 (4)	0.027 (4)	0.036 (4)	0.001 (4)	0.011 (3)	0.003 (4)
C14'	0.035 (4)	0.028 (4)	0.044 (4)	−0.005 (4)	0.020 (4)	0.000 (4)
C15'	0.042 (5)	0.034 (5)	0.036 (5)	0.003 (4)	0.009 (4)	−0.002 (4)
C16'	0.017 (4)	0.027 (4)	0.033 (4)	0.004 (3)	−0.003 (3)	0.000 (3)
C17'	0.021 (4)	0.022 (4)	0.025 (4)	0.000 (3)	0.015 (3)	0.002 (3)
C18'	0.035 (4)	0.032 (4)	0.022 (4)	−0.006 (3)	0.011 (3)	0.001 (3)

Geometric parameters (Å, º) top

S1—C1	1.673 (3)	C17—H17A	0.9900
N1—C1	1.381 (4)	C17—H17B	0.9900
N1—C2	1.390 (4)	C18—H18A	0.9900
N1—C3	1.439 (4)	C18—H18B	0.9900
N2—C2	1.301 (4)	C19—H19A	0.9900
N2—N3	1.387 (4)	C19—H19B	0.9900
N3—C1	1.347 (4)	C20—C21	1.514 (5)
N3—C19	1.478 (4)	C20—H20A	0.9900
N4—C19	1.447 (4)	C20—H20B	0.9900
N4—C20	1.462 (4)	C21—H21A	0.9900
N4—C23	1.460 (4)	C21—H21B	0.9900
N5—C24	1.418 (4)	C22—C23	1.525 (4)
N5—C21	1.468 (4)	C22—H22A	0.9900
N5—C22	1.468 (4)	C22—H22B	0.9900
C2—C9	1.546 (4)	C23—H23A	0.9900
C3—C4	1.382 (5)	C23—H23B	0.9900
C3—C8	1.378 (5)	C24—C25	1.400 (4)
C4—C5	1.403 (6)	C24—C29	1.403 (5)
C4—H4	0.9500	C25—C26	1.378 (5)
C5—C6	1.363 (8)	C25—H25	0.9500
C5—H5	0.9500	C26—C27	1.401 (5)
C6—C7	1.375 (7)	C26—H26	0.9500
C6—H6	0.9500	C27—C28	1.372 (5)
C7—C8	1.396 (5)	C27—H27	0.9500
C7—H7	0.9500	C28—C29	1.396 (5)
C8—H8	0.9500	C28—H28	0.9500
C9—C14	1.491 (2)	C29—H29	0.9500
C9—C18'	1.492 (2)	C10'—C11'	1.499 (2)
C9—C18	1.5111 (19)	C10'—H10C	0.9900
C9—C10'	1.512 (2)	C10'—H10D	0.9900
C9—C14'	1.512 (2)	C11'—C15'	1.501 (2)
C9—C10	1.518 (2)	C11'—C12'	1.501 (2)
C10—C11	1.503 (2)	C11'—H11B	1.0000
C10—H10A	0.9900	C12'—C13'	1.502 (2)
C10—H10B	0.9900	C12'—H12C	0.9900
C11—C12	1.502 (2)	C12'—H12D	0.9900
C11—C15	1.504 (2)	C13'—C14'	1.501 (2)
C11—H11	1.0000	C13'—C17'	1.501 (2)
C12—C13	1.502 (2)	C13'—H13'	1.0000
C12—H12A	0.9900	C14'—H14C	0.9900
C12—H12B	0.9900	C14'—H14D	0.9900
C13—C17	1.503 (2)	C15'—C16'	1.500 (2)
C13—C14	1.503 (2)	C15'—H15C	0.9900
C13—H13	1.0000	C15'—H15D	0.9900
C14—H14A	0.9900	C16'—C18'	1.499 (2)
C14—H14B	0.9900	C16'—C17'	1.501 (2)
C15—C16	1.504 (2)	C16'—H16'	1.0000
C15—H15A	0.9900	C17'—H17C	0.9900
C15—H15B	0.9900	C17'—H17D	0.9900
C16—C17	1.502 (2)	C18'—H18C	0.9900
C16—C18	1.505 (2)	C18'—H18D	0.9900
C16—H16	1.0000

C1—N1—C2	108.1 (2)	H18A—C18—H18B	108.2
C1—N1—C3	121.7 (3)	N4—C19—N3	116.3 (3)
C2—N1—C3	130.0 (3)	N4—C19—H19A	108.2
C2—N2—N3	105.4 (3)	N3—C19—H19A	108.2
C1—N3—N2	112.3 (2)	N4—C19—H19B	108.2
C1—N3—C19	129.8 (3)	N3—C19—H19B	108.2
N2—N3—C19	117.6 (3)	H19A—C19—H19B	107.4
C19—N4—C20	113.0 (3)	N4—C20—C21	110.2 (3)
C19—N4—C23	114.5 (3)	N4—C20—H20A	109.6
C20—N4—C23	110.8 (2)	C21—C20—H20A	109.6
C24—N5—C21	115.1 (2)	N4—C20—H20B	109.6
C24—N5—C22	115.6 (3)	C21—C20—H20B	109.6
C21—N5—C22	110.9 (3)	H20A—C20—H20B	108.1
N3—C1—N1	104.0 (3)	N5—C21—C20	110.6 (3)
N3—C1—S1	128.7 (2)	N5—C21—H21A	109.5
N1—C1—S1	127.3 (2)	C20—C21—H21A	109.5
N2—C2—N1	110.2 (3)	N5—C21—H21B	109.5
N2—C2—C9	122.7 (3)	C20—C21—H21B	109.5
N1—C2—C9	127.1 (3)	H21A—C21—H21B	108.1
C4—C3—C8	121.3 (3)	N5—C22—C23	109.1 (3)
C4—C3—N1	119.5 (3)	N5—C22—H22A	109.9
C8—C3—N1	119.2 (3)	C23—C22—H22A	109.9
C3—C4—C5	118.4 (4)	N5—C22—H22B	109.9
C3—C4—H4	120.8	C23—C22—H22B	109.9
C5—C4—H4	120.8	H22A—C22—H22B	108.3
C6—C5—C4	120.7 (4)	N4—C23—C22	109.8 (3)
C6—C5—H5	119.7	N4—C23—H23A	109.7
C4—C5—H5	119.7	C22—C23—H23A	109.7
C5—C6—C7	120.4 (4)	N4—C23—H23B	109.7
C5—C6—H6	119.8	C22—C23—H23B	109.7
C7—C6—H6	119.8	H23A—C23—H23B	108.2
C6—C7—C8	120.2 (5)	C25—C24—C29	118.2 (3)
C6—C7—H7	119.9	C25—C24—N5	118.9 (3)
C8—C7—H7	119.9	C29—C24—N5	122.9 (3)
C3—C8—C7	119.0 (4)	C26—C25—C24	120.9 (3)
C3—C8—H8	120.5	C26—C25—H25	119.5
C7—C8—H8	120.5	C24—C25—H25	119.5
C14—C9—C18'	113.4 (3)	C25—C26—C27	120.6 (3)
C14—C9—C18	112.7 (2)	C25—C26—H26	119.7
C18'—C9—C10'	108.8 (3)	C27—C26—H26	119.7
C18'—C9—C14'	110.4 (3)	C28—C27—C26	119.0 (3)
C10'—C9—C14'	104.2 (3)	C28—C27—H27	120.5
C14—C9—C10	108.7 (3)	C26—C27—H27	120.5
C18—C9—C10	105.9 (2)	C27—C28—C29	121.1 (3)
C14—C9—C2	112.6 (2)	C27—C28—H28	119.4
C18'—C9—C2	127.6 (3)	C29—C28—H28	119.4
C18—C9—C2	112.3 (2)	C28—C29—C24	120.2 (3)
C10'—C9—C2	102.9 (3)	C28—C29—H29	119.9
C14'—C9—C2	100.4 (3)	C24—C29—H29	119.9
C10—C9—C2	103.8 (2)	C11'—C10'—C9	111.7 (3)
C11—C10—C9	110.5 (2)	C11'—C10'—H10C	109.3
C11—C10—H10A	109.5	C9—C10'—H10C	109.3
C9—C10—H10A	109.5	C11'—C10'—H10D	109.3
C11—C10—H10B	109.5	C9—C10'—H10D	109.3
C9—C10—H10B	109.5	H10C—C10'—H10D	107.9
H10A—C10—H10B	108.1	C10'—C11'—C15'	109.6 (3)
C12—C11—C10	109.5 (3)	C10'—C11'—C12'	110.6 (3)
C12—C11—C15	109.1 (3)	C15'—C11'—C12'	109.1 (3)
C10—C11—C15	109.6 (3)	C10'—C11'—H11B	109.2
C12—C11—H11	109.5	C15'—C11'—H11B	109.2
C10—C11—H11	109.5	C12'—C11'—H11B	109.2
C15—C11—H11	109.5	C11'—C12'—C13'	108.0 (3)
C13—C12—C11	109.4 (2)	C11'—C12'—H12C	110.1
C13—C12—H12A	109.8	C13'—C12'—H12C	110.1
C11—C12—H12A	109.8	C11'—C12'—H12D	110.1
C13—C12—H12B	109.8	C13'—C12'—H12D	110.1
C11—C12—H12B	109.8	H12C—C12'—H12D	108.4
H12A—C12—H12B	108.2	C14'—C13'—C17'	108.8 (3)
C12—C13—C17	109.4 (3)	C14'—C13'—C12'	110.0 (3)
C12—C13—C14	109.9 (3)	C17'—C13'—C12'	109.2 (3)
C17—C13—C14	109.6 (3)	C14'—C13'—H13'	109.6
C12—C13—H13	109.3	C17'—C13'—H13'	109.6
C17—C13—H13	109.3	C12'—C13'—H13'	109.6
C14—C13—H13	109.3	C13'—C14'—C9	111.8 (3)
C9—C14—C13	109.1 (2)	C13'—C14'—H14C	109.3
C9—C14—H14A	109.9	C9—C14'—H14C	109.3
C13—C14—H14A	109.9	C13'—C14'—H14D	109.3
C9—C14—H14B	109.9	C9—C14'—H14D	109.3
C13—C14—H14B	109.9	H14C—C14'—H14D	107.9
H14A—C14—H14B	108.3	C16'—C15'—C11'	108.6 (3)
C11—C15—C16	108.8 (2)	C16'—C15'—H15C	110.0
C11—C15—H15A	109.9	C11'—C15'—H15C	110.0
C16—C15—H15A	109.9	C16'—C15'—H15D	110.0
C11—C15—H15B	109.9	C11'—C15'—H15D	110.0
C16—C15—H15B	109.9	H15C—C15'—H15D	108.3
H15A—C15—H15B	108.3	C18'—C16'—C15'	110.2 (3)
C17—C16—C15	109.9 (3)	C18'—C16'—C17'	109.5 (3)
C17—C16—C18	109.1 (3)	C15'—C16'—C17'	109.7 (3)
C15—C16—C18	109.5 (2)	C18'—C16'—H16'	109.1
C17—C16—H16	109.4	C15'—C16'—H16'	109.1
C15—C16—H16	109.4	C17'—C16'—H16'	109.1
C18—C16—H16	109.4	C16'—C17'—C13'	109.6 (3)
C13—C17—C16	110.0 (2)	C16'—C17'—H17C	109.7
C13—C17—H17A	109.7	C13'—C17'—H17C	109.7
C16—C17—H17A	109.7	C16'—C17'—H17D	109.7
C13—C17—H17B	109.7	C13'—C17'—H17D	109.7
C16—C17—H17B	109.7	H17C—C17'—H17D	108.2
H17A—C17—H17B	108.2	C9—C18'—C16'	110.3 (2)
C16—C18—C9	109.6 (2)	C9—C18'—H18C	109.6
C16—C18—H18A	109.7	C16'—C18'—H18C	109.6
C9—C18—H18A	109.7	C9—C18'—H18D	109.6
C16—C18—H18B	109.7	C16'—C18'—H18D	109.6
C9—C18—H18B	109.7	H18C—C18'—H18D	108.1

C2—N2—N3—C1	0.1 (3)	C18—C16—C17—C13	61.0 (3)
C2—N2—N3—C19	173.9 (3)	C17—C16—C18—C9	−57.2 (3)
N2—N3—C1—N1	0.1 (3)	C15—C16—C18—C9	63.1 (3)
C19—N3—C1—N1	−172.7 (3)	C14—C9—C18—C16	56.4 (3)
N2—N3—C1—S1	179.6 (2)	C10—C9—C18—C16	−62.4 (3)
C19—N3—C1—S1	6.8 (5)	C2—C9—C18—C16	−175.1 (3)
C2—N1—C1—N3	−0.2 (3)	C20—N4—C19—N3	−50.8 (4)
C3—N1—C1—N3	174.9 (3)	C23—N4—C19—N3	77.3 (4)
C2—N1—C1—S1	−179.7 (2)	C1—N3—C19—N4	−91.6 (4)
C3—N1—C1—S1	−4.6 (4)	N2—N3—C19—N4	95.9 (3)
N3—N2—C2—N1	−0.2 (3)	C19—N4—C20—C21	−172.1 (3)
N3—N2—C2—C9	179.8 (3)	C23—N4—C20—C21	57.8 (3)
C1—N1—C2—N2	0.2 (3)	C24—N5—C21—C20	−169.1 (3)
C3—N1—C2—N2	−174.3 (3)	C22—N5—C21—C20	57.3 (3)
C1—N1—C2—C9	−179.8 (3)	N4—C20—C21—N5	−56.3 (4)
C3—N1—C2—C9	5.7 (5)	C24—N5—C22—C23	168.3 (3)
C1—N1—C3—C4	91.4 (4)	C21—N5—C22—C23	−58.3 (3)
C2—N1—C3—C4	−94.7 (4)	C19—N4—C23—C22	171.3 (3)
C1—N1—C3—C8	−88.0 (4)	C20—N4—C23—C22	−59.5 (3)
C2—N1—C3—C8	85.9 (5)	N5—C22—C23—N4	59.2 (3)
C8—C3—C4—C5	−0.7 (6)	C21—N5—C24—C25	57.9 (4)
N1—C3—C4—C5	179.9 (4)	C22—N5—C24—C25	−170.7 (3)
C3—C4—C5—C6	0.0 (7)	C21—N5—C24—C29	−123.8 (3)
C4—C5—C6—C7	0.2 (8)	C22—N5—C24—C29	7.5 (4)
C5—C6—C7—C8	0.3 (8)	C29—C24—C25—C26	0.1 (5)
C4—C3—C8—C7	1.2 (7)	N5—C24—C25—C26	178.4 (3)
N1—C3—C8—C7	−179.4 (4)	C24—C25—C26—C27	0.1 (5)
C6—C7—C8—C3	−1.0 (7)	C25—C26—C27—C28	−0.5 (5)
N2—C2—C9—C14	−9.7 (4)	C26—C27—C28—C29	0.7 (5)
N1—C2—C9—C14	170.3 (3)	C27—C28—C29—C24	−0.6 (5)
N2—C2—C9—C18'	140.3 (4)	C25—C24—C29—C28	0.1 (4)
N1—C2—C9—C18'	−39.7 (5)	N5—C24—C29—C28	−178.1 (3)
N2—C2—C9—C18	−138.3 (3)	C18'—C9—C10'—C11'	57.1 (4)
N1—C2—C9—C18	41.8 (4)	C14'—C9—C10'—C11'	−60.7 (4)
N2—C2—C9—C10'	13.7 (4)	C2—C9—C10'—C11'	−165.1 (4)
N1—C2—C9—C10'	−166.2 (4)	C9—C10'—C11'—C15'	−58.3 (4)
N2—C2—C9—C14'	−93.6 (4)	C9—C10'—C11'—C12'	62.0 (4)
N1—C2—C9—C14'	86.5 (4)	C10'—C11'—C12'—C13'	−57.6 (4)
N2—C2—C9—C10	107.7 (3)	C15'—C11'—C12'—C13'	63.1 (4)
N1—C2—C9—C10	−72.2 (4)	C11'—C12'—C13'—C14'	57.6 (4)
C14—C9—C10—C11	−59.7 (3)	C11'—C12'—C13'—C17'	−61.8 (4)
C18—C9—C10—C11	61.7 (3)	C17'—C13'—C14'—C9	57.0 (4)
C2—C9—C10—C11	−179.8 (3)	C12'—C13'—C14'—C9	−62.6 (4)
C9—C10—C11—C12	58.5 (3)	C14—C9—C14'—C13'	56.1 (4)
C9—C10—C11—C15	−61.1 (3)	C18'—C9—C14'—C13'	−55.5 (4)
C10—C11—C12—C13	−58.4 (4)	C10'—C9—C14'—C13'	61.2 (4)
C15—C11—C12—C13	61.6 (3)	C2—C9—C14'—C13'	167.5 (4)
C11—C12—C13—C17	−60.0 (3)	C10'—C11'—C15'—C16'	59.0 (4)
C11—C12—C13—C14	60.3 (4)	C12'—C11'—C15'—C16'	−62.2 (4)
C18—C9—C14—C13	−56.6 (4)	C11'—C15'—C16'—C18'	−60.8 (4)
C10—C9—C14—C13	60.5 (3)	C11'—C15'—C16'—C17'	59.9 (4)
C2—C9—C14—C13	175.1 (3)	C18'—C16'—C17'—C13'	61.9 (4)
C12—C13—C14—C9	−61.8 (4)	C15'—C16'—C17'—C13'	−59.2 (4)
C17—C13—C14—C9	58.4 (4)	C14'—C13'—C17'—C16'	−60.0 (4)
C12—C11—C15—C16	−61.3 (3)	C12'—C13'—C17'—C16'	60.1 (4)
C10—C11—C15—C16	58.6 (3)	C10'—C9—C18'—C16'	−57.6 (4)
C11—C15—C16—C17	60.1 (3)	C14'—C9—C18'—C16'	56.1 (4)
C11—C15—C16—C18	−59.7 (3)	C2—C9—C18'—C16'	178.2 (3)
C12—C13—C17—C16	58.7 (3)	C15'—C16'—C18'—C9	61.0 (4)
C14—C13—C17—C16	−61.9 (3)	C17'—C16'—C18'—C9	−59.8 (4)
C15—C16—C17—C13	−59.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···S1ⁱ	0.99	2.84	3.593 (4)	133

Symmetry code: (i) −x+2, y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₉H₃₅N₅S
M_r	485.68
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	11.3342 (5), 8.4744 (3), 13.7868 (6)
β (°)	103.864 (4)
V (Å³)	1285.65 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.40 × 0.35 × 0.30

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.941, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	8952, 5539, 5155
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.154, 1.02
No. of reflections	5537
No. of parameters	398
No. of restraints	169
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.56
Absolute structure	Flack (1983), 2382 Friedel pairs
Absolute structure parameter	0.01 (11)

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···S1ⁱ	0.99	2.84	3.593 (4)	133

Symmetry code: (i) −x+2, y+1/2, −z.

Acknowledgements

We thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
El-Emam, A. A. & Ibrahim, T. M. (1991). Arzneim. Forsch./Drug Res. 41, 1260–1264. CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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 2| February 2012| Page o345

doi:10.1107/S1600536811055711

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

3-(Adamantan-1-yl)-4-phenyl-1-[(4-phenyl­piperazin-1-yl)meth­yl]-1H-1,2,4-triazole-5(4H)-thione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-(Adamantan-1-yl)-4-phenyl-1-[(4-phenylpiperazin-1-yl)methyl]-1H-1,2,4-triazole-5(4H)-thione