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

Al-Abdullah, E.S.; Al-Tuwaijri, H.M.; El-Emam, A.A.; Chidan Kumar, C.S.; Fun, H.-K.

doi:10.1107/S1600536813031127

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1813-o1814

doi:10.1107/S1600536813031127

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

Ebtehal S. Al-Abdullah,^a Hanaa M. Al-Tuwaijri,^a Ali A. El-Emam,^a ‡ C. S. Chidan Kumar ^b and Hoong-Kun Fun ^a ^*§

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riaydh 11451, Saudi Arabia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hfun.c@ksu.edu.sa

(Received 12 November 2013; accepted 12 November 2013; online 23 November 2013)

In the title compound, C₂₆H₃₇N₅S, the piperazine ring adopts a chair conformation with the exocyclic N—C bonds in pseudo-equatorial orientations. The piperazine ring (all atoms) subtends dihedral angles of 79.47 (9) and 73.07 (9)° with the triazole and benzene rings, respectively, resulting in an approximate U-shape for the molecule. No significant intermolecular interactions are observed in the crystal.

CCDC reference: 971638

Related literature

For the pharmacological properties of adamantane derivatives and adamantyl-1,2,4-triazoles, see: Vernier et al. (1969 ); El-Emam et al. (2004 , 2013 ); Al-Deeb et al. (2006 ); Kadi et al. (2007 , 2010 ). For related adamantyl-1,2,4-triazole structures, see: Al-Tamimi et al. (2010 ); Al-Abdullah et al. (2012 ); El-Emam et al. (2012 ). For the synthesis of the starting material, see El-Emam & Ibrahim (1991 ). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₆H₃₇N₅S
M_r = 451.67
Triclinic, $[P \overline 1]$
a = 10.5618 (2) Å
b = 11.2123 (2) Å
c = 11.3084 (2) Å
α = 89.974 (1)°
β = 77.619 (1)°
γ = 70.842 (1)°
V = 1232.03 (4) Å³
Z = 2
Cu Kα radiation
μ = 1.33 mm⁻¹
T = 296 K
0.69 × 0.51 × 0.39 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.460, T_max = 0.626
13169 measured reflections
4319 independent reflections
3986 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.117
S = 1.08
4319 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 971638

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813031127/hb7161sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813031127/hb7161Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813031127/hb7161Isup3.cml

checkCIF report

Comment top

Adamantane derivatives were early recognized for their diverse biological activities including antiviral activity against the influenza (Vernier et al., 1969) and HIV viruses (El-Emam et al., 2004). In addition, adamantane derivatives were reported to exhibit marked antibacterial (Kadi et al., 2007, 2010) and anti-inflammatory (El-Emam & Ibrahim, 1991) activities. In continuation of our interest in this area, we now describe the synthesis and structure of the title compound, (I).

The piperazine ring (N1/N2/C8–C11) ring, Fig. 1, adopts a chair conformation, with puckering parameters: Q = 0.5829 (17) Å, θ = 176.42 (17)°, and ϕ = 221 (3)° (Cremer & Pople, 1975) and a maximum deviation of 0.257 (1) Å at atom N1. The dihedral angle between the piperazine ring and the triazole (N3–N5/C13/C16) ring is 79.47 (9)°. The triazole (N3–N5/C13/C16) ring forms the dihedral angle of 53.07 (10)° with the benzene (C1–C6) ring. In the crystal, no significant intermolecular interactions beyond the expected packing contacts are observed.

Related literature top

For the pharmacological properties of adamantane derivatives and adamantyl-1,2,4-triazoles, see: Vernier et al. (1969); El-Emam et al. (2004, 2013); Al-Deeb et al. (2006); Kadi et al. (2007, 2010). For related adamantyl-1,2,4-triazole structures, see: Al-Tamimi et al. (2010); Al-Abdullah et al. (2012); El-Emam et al. (2012). For further details of the synthesis, see El-Emam & Ibrahim (1991). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975).

Experimental top

A mixture of 527 mg (2 mmol) of 3-(1-adamantyl)-4-ethyl-4H-1,2,4- triazole-5-thiol (El-Emam et al., 1991), 1-benzylpiperazine (353 mg, 2 mmol) and 37% formaldehyde solution (1 ml), in ethanol (8 ml), was heated under reflux for 15 min until a clear solution was obtained. Stirring was continued for 12 h at room temperature and the mixture was allowed to stand overnight. Cold water (5 ml) was slowly 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 759 mg (84%) of the title compound (C₂₆H₃₇N₅S) as crystals. m.p.: 441–443 K. Single crystals suitable for X-ray analysis were recrystallized from CHCl₃:EtOH solution (1:1; 5 ml) through slow evaporation at room temperature.

¹H NMR (CDCl₃, 500.13 MHz): δ 1.13 (t, 3H, CH₂CH₃, J = 6.0 Hz), 1.68–1.73 (m, 6H, Adamantane-H), 1.98–2.10 (m, 9H, Adamantane-H), 2.72–2.76 (m, 4H, Piperazine-H), 3.24–3.26 (m, 4H, Piperazine-H), 3.72 (s, 2H, Benzylic-CH₂), 4.15 (q, 2H, CH₂CH₃, J = 6.5 Hz), 5.02 (s, 2H, CH₂), 7.20–7.54 (m, 5H, Ar—H). ¹³C NMR (CDCl₃, 125.76 MHz): δ 12.74 (CH₂CH₃), 26.90, 34.36, 35.26, 38.82 (Adamantane-C), 40.62 (CH₂CH₃), 46.01, 50.37 (Piperazine-C), 61.59 (Benzylic-CH2), 66.66 (CH₂), 127.40, 128.31, 129.19, 130.57 (Ar—C), 155.55 (Triazole C-5), 167.73 (C=S).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids.

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

Crystal data top

C₂₆H₃₇N₅S	Z = 2
M_r = 451.67	F(000) = 488
Triclinic, P1	D_x = 1.218 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 10.5618 (2) Å	Cell parameters from 6190 reflections
b = 11.2123 (2) Å	θ = 4.0–69.3°
c = 11.3084 (2) Å	µ = 1.33 mm⁻¹
α = 89.974 (1)°	T = 296 K
β = 77.619 (1)°	Block, colourless
γ = 70.842 (1)°	0.69 × 0.51 × 0.39 mm
V = 1232.03 (4) Å³

Data collection top

Bruker APEXII CCD diffractometer	4319 independent reflections
Radiation source: fine-focus sealed tube	3986 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 67.5°, θ_min = 4.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.460, T_max = 0.626	k = −13→13
13169 measured reflections	l = −12→10

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)] = 0.040	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0605P)² + 0.2192P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
4319 reflections	Δρ_max = 0.22 e Å⁻³
291 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (5)

Crystal data top

C₂₆H₃₇N₅S	γ = 70.842 (1)°
M_r = 451.67	V = 1232.03 (4) Å³
Triclinic, P1	Z = 2
a = 10.5618 (2) Å	Cu Kα radiation
b = 11.2123 (2) Å	µ = 1.33 mm⁻¹
c = 11.3084 (2) Å	T = 296 K
α = 89.974 (1)°	0.69 × 0.51 × 0.39 mm
β = 77.619 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4319 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3986 reflections with I > 2σ(I)
T_min = 0.460, T_max = 0.626	R_int = 0.025
13169 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.08	Δρ_max = 0.22 e Å⁻³
4319 reflections	Δρ_min = −0.19 e Å⁻³
291 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
S1	0.22677 (5)	0.18527 (4)	0.13850 (5)	0.06851 (17)
N1	−0.34170 (12)	0.23635 (12)	0.02812 (11)	0.0489 (3)
N2	−0.16540 (13)	0.16685 (11)	0.19435 (11)	0.0477 (3)
N3	−0.03907 (13)	0.29271 (11)	0.26359 (12)	0.0486 (3)
N4	−0.13337 (13)	0.40759 (11)	0.31410 (11)	0.0485 (3)
N5	0.06528 (12)	0.42739 (11)	0.22592 (12)	0.0476 (3)
C1	−0.3188 (2)	0.16668 (18)	−0.27179 (17)	0.0688 (5)
H1A	−0.2913	0.0807	−0.2598	0.083*
C2	−0.2848 (2)	0.2056 (2)	−0.38571 (18)	0.0802 (6)
H2A	−0.2331	0.1456	−0.4498	0.096*
C3	−0.3260 (2)	0.3322 (2)	−0.40656 (17)	0.0704 (5)
H3A	−0.3028	0.3579	−0.4841	0.084*
C4	−0.4019 (2)	0.41987 (18)	−0.31105 (17)	0.0654 (4)
H4A	−0.4310	0.5056	−0.3240	0.078*
C5	−0.43506 (17)	0.38159 (17)	−0.19630 (16)	0.0599 (4)
H5A	−0.4859	0.4419	−0.1323	0.072*
C6	−0.39358 (15)	0.25397 (16)	−0.17470 (15)	0.0537 (4)
C7	−0.42804 (17)	0.21280 (18)	−0.04912 (16)	0.0594 (4)
H7A	−0.5240	0.2581	−0.0122	0.071*
H7B	−0.4154	0.1231	−0.0542	0.071*
C8	−0.39368 (16)	0.21841 (17)	0.15458 (15)	0.0567 (4)
H8A	−0.3900	0.1312	0.1624	0.068*
H8B	−0.4889	0.2726	0.1813	0.068*
C9	−0.30821 (16)	0.25001 (16)	0.23323 (15)	0.0560 (4)
H9A	−0.3131	0.3376	0.2266	0.067*
H9B	−0.3441	0.2393	0.3175	0.067*
C10	−0.11059 (15)	0.17746 (15)	0.06677 (14)	0.0524 (4)
H10A	−0.0178	0.1175	0.0415	0.063*
H10B	−0.1064	0.2620	0.0557	0.063*
C11	−0.20000 (16)	0.15135 (17)	−0.01097 (16)	0.0578 (4)
H11A	−0.1641	0.1624	−0.0951	0.069*
H11B	−0.1976	0.0643	−0.0054	0.069*
C12	−0.07720 (17)	0.17719 (14)	0.27078 (15)	0.0517 (4)
H12A	0.0066	0.1044	0.2506	0.062*
H12B	−0.1222	0.1729	0.3542	0.062*
C13	0.08395 (16)	0.30056 (14)	0.20895 (14)	0.0492 (3)
C14	0.17668 (16)	0.47676 (15)	0.17788 (17)	0.0597 (4)
H14A	0.2618	0.4197	0.1937	0.072*
H14B	0.1571	0.5583	0.2201	0.072*
C15	0.1955 (2)	0.49166 (19)	0.04371 (19)	0.0760 (5)
H15A	0.2609	0.5345	0.0186	0.114*
H15B	0.1090	0.5404	0.0264	0.114*
H15C	0.2287	0.4097	0.0006	0.114*
C16	−0.06822 (15)	0.48847 (13)	0.28983 (13)	0.0449 (3)
C17	−0.13467 (15)	0.62762 (13)	0.33107 (14)	0.0464 (3)
C18	−0.07200 (18)	0.66332 (15)	0.43095 (16)	0.0575 (4)
H18A	−0.0833	0.6123	0.4991	0.069*
H18B	0.0257	0.6464	0.3997	0.069*
C19	−0.1432 (2)	0.80408 (16)	0.47337 (18)	0.0678 (5)
H19A	−0.1015	0.8264	0.5357	0.081*
C20	−0.1263 (2)	0.88384 (16)	0.3662 (2)	0.0720 (5)
H20A	−0.1692	0.9730	0.3933	0.086*
H20B	−0.0292	0.8678	0.3323	0.086*
C21	−0.1921 (2)	0.85163 (16)	0.27002 (18)	0.0675 (5)
H21A	−0.1816	0.9042	0.2018	0.081*
C22	−0.3438 (2)	0.87674 (18)	0.3226 (2)	0.0792 (6)
H22A	−0.3861	0.8562	0.2608	0.095*
H22B	−0.3893	0.9657	0.3495	0.095*
C23	−0.36012 (19)	0.79624 (18)	0.4289 (2)	0.0737 (5)
H23A	−0.4583	0.8124	0.4628	0.088*
C24	−0.28947 (17)	0.65544 (16)	0.38466 (19)	0.0651 (5)
H24A	−0.3317	0.6342	0.3233	0.078*
H24B	−0.3014	0.6036	0.4520	0.078*
C25	−0.2958 (2)	0.82930 (19)	0.5263 (2)	0.0783 (6)
H25A	−0.3071	0.7784	0.5946	0.094*
H25B	−0.3409	0.9178	0.5550	0.094*
C26	−0.12118 (19)	0.71224 (15)	0.22511 (15)	0.0579 (4)
H26A	−0.0246	0.6969	0.1894	0.069*
H26B	−0.1627	0.6914	0.1630	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0597 (3)	0.0421 (2)	0.0933 (4)	−0.01144 (18)	−0.0046 (2)	−0.0041 (2)
N1	0.0435 (6)	0.0499 (7)	0.0504 (7)	−0.0141 (5)	−0.0069 (5)	0.0036 (5)
N2	0.0565 (7)	0.0367 (6)	0.0529 (7)	−0.0188 (5)	−0.0140 (5)	0.0067 (5)
N3	0.0568 (7)	0.0347 (6)	0.0569 (7)	−0.0198 (5)	−0.0113 (5)	0.0030 (5)
N4	0.0538 (7)	0.0387 (6)	0.0552 (7)	−0.0200 (5)	−0.0097 (5)	0.0024 (5)
N5	0.0475 (6)	0.0368 (6)	0.0607 (8)	−0.0178 (5)	−0.0112 (5)	0.0029 (5)
C1	0.0811 (12)	0.0559 (10)	0.0660 (11)	−0.0199 (9)	−0.0143 (9)	−0.0018 (8)
C2	0.1022 (15)	0.0737 (13)	0.0568 (11)	−0.0282 (11)	−0.0035 (10)	−0.0116 (9)
C3	0.0840 (12)	0.0775 (13)	0.0564 (10)	−0.0368 (10)	−0.0149 (9)	0.0063 (8)
C4	0.0700 (11)	0.0592 (10)	0.0710 (12)	−0.0235 (9)	−0.0213 (9)	0.0071 (8)
C5	0.0556 (9)	0.0596 (10)	0.0609 (10)	−0.0164 (8)	−0.0103 (7)	−0.0049 (7)
C6	0.0463 (8)	0.0607 (9)	0.0573 (9)	−0.0200 (7)	−0.0152 (6)	0.0018 (7)
C7	0.0519 (8)	0.0691 (11)	0.0614 (10)	−0.0258 (8)	−0.0132 (7)	0.0068 (8)
C8	0.0502 (8)	0.0644 (10)	0.0552 (9)	−0.0231 (7)	−0.0052 (7)	0.0060 (7)
C9	0.0550 (9)	0.0611 (10)	0.0500 (9)	−0.0230 (7)	−0.0024 (7)	0.0006 (7)
C10	0.0444 (7)	0.0501 (8)	0.0556 (9)	−0.0092 (6)	−0.0070 (6)	0.0005 (6)
C11	0.0489 (8)	0.0602 (10)	0.0550 (9)	−0.0087 (7)	−0.0072 (7)	−0.0058 (7)
C12	0.0667 (9)	0.0372 (7)	0.0594 (9)	−0.0247 (7)	−0.0200 (7)	0.0123 (6)
C13	0.0552 (8)	0.0384 (7)	0.0572 (9)	−0.0184 (6)	−0.0151 (7)	0.0047 (6)
C14	0.0478 (8)	0.0450 (8)	0.0874 (12)	−0.0212 (7)	−0.0089 (8)	0.0019 (7)
C15	0.0716 (11)	0.0614 (11)	0.0862 (14)	−0.0250 (9)	0.0045 (10)	0.0112 (9)
C16	0.0489 (7)	0.0374 (7)	0.0520 (8)	−0.0176 (6)	−0.0138 (6)	0.0041 (6)
C17	0.0483 (8)	0.0351 (7)	0.0580 (9)	−0.0152 (6)	−0.0145 (6)	0.0027 (6)
C18	0.0659 (10)	0.0455 (8)	0.0632 (10)	−0.0149 (7)	−0.0251 (8)	0.0019 (7)
C19	0.0816 (12)	0.0502 (9)	0.0746 (12)	−0.0187 (9)	−0.0292 (9)	−0.0094 (8)
C20	0.0787 (12)	0.0377 (8)	0.0997 (15)	−0.0230 (8)	−0.0151 (10)	−0.0030 (8)
C21	0.0830 (12)	0.0408 (9)	0.0741 (12)	−0.0137 (8)	−0.0196 (9)	0.0138 (8)
C22	0.0741 (12)	0.0502 (10)	0.1061 (16)	−0.0029 (9)	−0.0337 (11)	0.0037 (10)
C23	0.0524 (9)	0.0517 (10)	0.1044 (15)	−0.0100 (8)	−0.0034 (9)	−0.0068 (9)
C24	0.0525 (9)	0.0500 (9)	0.0910 (13)	−0.0194 (7)	−0.0088 (8)	−0.0014 (8)
C25	0.0895 (14)	0.0522 (10)	0.0762 (13)	−0.0130 (10)	−0.0006 (10)	−0.0086 (8)
C26	0.0698 (10)	0.0446 (8)	0.0587 (10)	−0.0164 (7)	−0.0180 (8)	0.0071 (7)

Geometric parameters (Å, º) top

S1—C13	1.6694 (16)	C11—H11B	0.9700
N1—C8	1.457 (2)	C12—H12A	0.9700
N1—C11	1.4574 (19)	C12—H12B	0.9700
N1—C7	1.471 (2)	C14—C15	1.504 (3)
N2—C12	1.4299 (19)	C14—H14A	0.9700
N2—C10	1.455 (2)	C14—H14B	0.9700
N2—C9	1.460 (2)	C15—H15A	0.9600
N3—C13	1.345 (2)	C15—H15B	0.9600
N3—N4	1.3756 (17)	C15—H15C	0.9600
N3—C12	1.4746 (18)	C16—C17	1.5119 (19)
N4—C16	1.3037 (18)	C17—C18	1.539 (2)
N5—C13	1.3777 (18)	C17—C26	1.540 (2)
N5—C16	1.3817 (19)	C17—C24	1.542 (2)
N5—C14	1.463 (2)	C18—C19	1.534 (2)
C1—C2	1.372 (3)	C18—H18A	0.9700
C1—C6	1.382 (2)	C18—H18B	0.9700
C1—H1A	0.9300	C19—C20	1.520 (3)
C2—C3	1.378 (3)	C19—C25	1.523 (3)
C2—H2A	0.9300	C19—H19A	0.9800
C3—C4	1.374 (3)	C20—C21	1.512 (3)
C3—H3A	0.9300	C20—H20A	0.9700
C4—C5	1.376 (3)	C20—H20B	0.9700
C4—H4A	0.9300	C21—C22	1.515 (3)
C5—C6	1.390 (2)	C21—C26	1.527 (2)
C5—H5A	0.9300	C21—H21A	0.9800
C6—C7	1.500 (2)	C22—C23	1.518 (3)
C7—H7A	0.9700	C22—H22A	0.9700
C7—H7B	0.9700	C22—H22B	0.9700
C8—C9	1.512 (2)	C23—C25	1.516 (3)
C8—H8A	0.9700	C23—C24	1.539 (2)
C8—H8B	0.9700	C23—H23A	0.9800
C9—H9A	0.9700	C24—H24A	0.9700
C9—H9B	0.9700	C24—H24B	0.9700
C10—C11	1.513 (2)	C25—H25A	0.9700
C10—H10A	0.9700	C25—H25B	0.9700
C10—H10B	0.9700	C26—H26A	0.9700
C11—H11A	0.9700	C26—H26B	0.9700

C8—N1—C11	108.65 (12)	N5—C14—H14B	109.1
C8—N1—C7	110.90 (12)	C15—C14—H14B	109.1
C11—N1—C7	110.90 (13)	H14A—C14—H14B	107.8
C12—N2—C10	113.10 (12)	C14—C15—H15A	109.5
C12—N2—C9	114.96 (12)	C14—C15—H15B	109.5
C10—N2—C9	110.90 (12)	H15A—C15—H15B	109.5
C13—N3—N4	112.98 (11)	C14—C15—H15C	109.5
C13—N3—C12	126.34 (13)	H15A—C15—H15C	109.5
N4—N3—C12	120.67 (12)	H15B—C15—H15C	109.5
C16—N4—N3	104.98 (12)	N4—C16—N5	110.22 (12)
C13—N5—C16	108.38 (12)	N4—C16—C17	122.45 (13)
C13—N5—C14	120.92 (13)	N5—C16—C17	127.32 (12)
C16—N5—C14	130.70 (12)	C16—C17—C18	110.91 (12)
C2—C1—C6	120.65 (18)	C16—C17—C26	111.94 (13)
C2—C1—H1A	119.7	C18—C17—C26	109.46 (13)
C6—C1—H1A	119.7	C16—C17—C24	108.86 (12)
C1—C2—C3	120.97 (18)	C18—C17—C24	107.90 (14)
C1—C2—H2A	119.5	C26—C17—C24	107.63 (13)
C3—C2—H2A	119.5	C19—C18—C17	109.97 (13)
C4—C3—C2	118.94 (18)	C19—C18—H18A	109.7
C4—C3—H3A	120.5	C17—C18—H18A	109.7
C2—C3—H3A	120.5	C19—C18—H18B	109.7
C3—C4—C5	120.39 (18)	C17—C18—H18B	109.7
C3—C4—H4A	119.8	H18A—C18—H18B	108.2
C5—C4—H4A	119.8	C20—C19—C25	109.56 (16)
C4—C5—C6	120.91 (16)	C20—C19—C18	109.55 (15)
C4—C5—H5A	119.5	C25—C19—C18	109.49 (16)
C6—C5—H5A	119.5	C20—C19—H19A	109.4
C1—C6—C5	118.12 (16)	C25—C19—H19A	109.4
C1—C6—C7	121.14 (16)	C18—C19—H19A	109.4
C5—C6—C7	120.73 (15)	C21—C20—C19	109.95 (15)
N1—C7—C6	112.00 (13)	C21—C20—H20A	109.7
N1—C7—H7A	109.2	C19—C20—H20A	109.7
C6—C7—H7A	109.2	C21—C20—H20B	109.7
N1—C7—H7B	109.2	C19—C20—H20B	109.7
C6—C7—H7B	109.2	H20A—C20—H20B	108.2
H7A—C7—H7B	107.9	C20—C21—C22	109.80 (17)
N1—C8—C9	110.02 (13)	C20—C21—C26	109.38 (14)
N1—C8—H8A	109.7	C22—C21—C26	109.75 (16)
C9—C8—H8A	109.7	C20—C21—H21A	109.3
N1—C8—H8B	109.7	C22—C21—H21A	109.3
C9—C8—H8B	109.7	C26—C21—H21A	109.3
H8A—C8—H8B	108.2	C21—C22—C23	109.30 (15)
N2—C9—C8	109.63 (13)	C21—C22—H22A	109.8
N2—C9—H9A	109.7	C23—C22—H22A	109.8
C8—C9—H9A	109.7	C21—C22—H22B	109.8
N2—C9—H9B	109.7	C23—C22—H22B	109.8
C8—C9—H9B	109.7	H22A—C22—H22B	108.3
H9A—C9—H9B	108.2	C25—C23—C22	109.94 (17)
N2—C10—C11	110.69 (13)	C25—C23—C24	109.75 (16)
N2—C10—H10A	109.5	C22—C23—C24	109.33 (17)
C11—C10—H10A	109.5	C25—C23—H23A	109.3
N2—C10—H10B	109.5	C22—C23—H23A	109.3
C11—C10—H10B	109.5	C24—C23—H23A	109.3
H10A—C10—H10B	108.1	C23—C24—C17	110.23 (14)
N1—C11—C10	110.90 (13)	C23—C24—H24A	109.6
N1—C11—H11A	109.5	C17—C24—H24A	109.6
C10—C11—H11A	109.5	C23—C24—H24B	109.6
N1—C11—H11B	109.5	C17—C24—H24B	109.6
C10—C11—H11B	109.5	H24A—C24—H24B	108.1
H11A—C11—H11B	108.0	C23—C25—C19	109.13 (16)
N2—C12—N3	116.03 (12)	C23—C25—H25A	109.9
N2—C12—H12A	108.3	C19—C25—H25A	109.9
N3—C12—H12A	108.3	C23—C25—H25B	109.9
N2—C12—H12B	108.3	C19—C25—H25B	109.9
N3—C12—H12B	108.3	H25A—C25—H25B	108.3
H12A—C12—H12B	107.4	C21—C26—C17	110.28 (14)
N3—C13—N5	103.43 (13)	C21—C26—H26A	109.6
N3—C13—S1	128.88 (11)	C17—C26—H26A	109.6
N5—C13—S1	127.69 (12)	C21—C26—H26B	109.6
N5—C14—C15	112.60 (15)	C17—C26—H26B	109.6
N5—C14—H14A	109.1	H26A—C26—H26B	108.1
C15—C14—H14A	109.1

C13—N3—N4—C16	0.40 (16)	N3—N4—C16—C17	−179.14 (13)
C12—N3—N4—C16	−178.80 (13)	C13—N5—C16—N4	0.30 (17)
C6—C1—C2—C3	−1.0 (3)	C14—N5—C16—N4	179.45 (15)
C1—C2—C3—C4	0.2 (3)	C13—N5—C16—C17	178.95 (14)
C2—C3—C4—C5	0.5 (3)	C14—N5—C16—C17	−1.9 (3)
C3—C4—C5—C6	−0.5 (3)	N4—C16—C17—C18	109.96 (16)
C2—C1—C6—C5	1.1 (3)	N5—C16—C17—C18	−68.55 (19)
C2—C1—C6—C7	−178.28 (18)	N4—C16—C17—C26	−127.47 (15)
C4—C5—C6—C1	−0.3 (3)	N5—C16—C17—C26	54.03 (19)
C4—C5—C6—C7	179.02 (15)	N4—C16—C17—C24	−8.6 (2)
C8—N1—C7—C6	169.20 (14)	N5—C16—C17—C24	172.88 (15)
C11—N1—C7—C6	−69.99 (18)	C16—C17—C18—C19	−178.70 (14)
C1—C6—C7—N1	104.19 (18)	C26—C17—C18—C19	57.30 (18)
C5—C6—C7—N1	−75.16 (19)	C24—C17—C18—C19	−59.55 (18)
C11—N1—C8—C9	60.95 (17)	C17—C18—C19—C20	−58.9 (2)
C7—N1—C8—C9	−176.91 (14)	C17—C18—C19—C25	61.3 (2)
C12—N2—C9—C8	−172.94 (12)	C25—C19—C20—C21	−59.28 (19)
C10—N2—C9—C8	57.20 (16)	C18—C19—C20—C21	60.8 (2)
N1—C8—C9—N2	−60.32 (17)	C19—C20—C21—C22	59.44 (19)
C12—N2—C10—C11	173.70 (12)	C19—C20—C21—C26	−61.1 (2)
C9—N2—C10—C11	−55.46 (16)	C20—C21—C22—C23	−59.6 (2)
C8—N1—C11—C10	−59.08 (18)	C26—C21—C22—C23	60.7 (2)
C7—N1—C11—C10	178.79 (13)	C21—C22—C23—C25	60.2 (2)
N2—C10—C11—N1	56.68 (18)	C21—C22—C23—C24	−60.4 (2)
C10—N2—C12—N3	55.67 (17)	C25—C23—C24—C17	−60.1 (2)
C9—N2—C12—N3	−73.11 (17)	C22—C23—C24—C17	60.5 (2)
C13—N3—C12—N2	−105.86 (17)	C16—C17—C24—C23	179.36 (15)
N4—N3—C12—N2	73.21 (18)	C18—C17—C24—C23	58.92 (19)
N4—N3—C13—N5	−0.21 (16)	C26—C17—C24—C23	−59.11 (19)
C12—N3—C13—N5	178.92 (13)	C22—C23—C25—C19	−60.1 (2)
N4—N3—C13—S1	179.12 (11)	C24—C23—C25—C19	60.2 (2)
C12—N3—C13—S1	−1.7 (2)	C20—C19—C25—C23	59.33 (19)
C16—N5—C13—N3	−0.04 (16)	C18—C19—C25—C23	−60.8 (2)
C14—N5—C13—N3	−179.29 (14)	C20—C21—C26—C17	59.6 (2)
C16—N5—C13—S1	−179.39 (12)	C22—C21—C26—C17	−60.88 (19)
C14—N5—C13—S1	1.4 (2)	C16—C17—C26—C21	178.81 (13)
C13—N5—C14—C15	77.74 (18)	C18—C17—C26—C21	−57.80 (18)
C16—N5—C14—C15	−101.32 (19)	C24—C17—C26—C21	59.22 (18)
N3—N4—C16—N5	−0.41 (15)

Experimental details

Crystal data
Chemical formula	C₂₆H₃₇N₅S
M_r	451.67
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.5618 (2), 11.2123 (2), 11.3084 (2)
α, β, γ (°)	89.974 (1), 77.619 (1), 70.842 (1)
V (Å³)	1232.03 (4)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.33
Crystal size (mm)	0.69 × 0.51 × 0.39

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.460, 0.626
No. of measured, independent and observed [I > 2σ(I)] reflections	13169, 4319, 3986
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.117, 1.08
No. of reflections	4319
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Footnotes

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

§Thomson Reuters ResearcherID: A-3561-2009

Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center for Female Scientific and Medical Colleges, King Saud University, is greatly appreciated. CSCK thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

References

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