3-(Adamantan-1-yl)-4-benzyl-1H-1,2,4-triazole-5(4H)-thione

Al-Omary, F.A.M.; Ghabbour, H.A.; El-Emam, A.A.; Chidan Kumar, C.S.; Fun, H.-K.

doi:10.1107/S1600536814013257

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 7| July 2014| Pages o766-o767

https://doi.org/10.1107/S1600536814013257

Open

access

3-(Adamantan-1-yl)-4-benzyl-1H-1,2,4-triazole-5(4H)-thione

Fatmah A. M. Al-Omary,^a Hazem A. Ghabbour,^a Ali A. El-Emam,^a,^b ^* C. S. Chidan Kumar ^c ‡ and Hoong-Kun Fun ^a,^c ^*§

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riaydh 11451, Saudi Arabia, ^bKing Abdullah Institute for Nanotechnology (KAIN), King Saud University, Riyadh 11451, Saudi Arabia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: elemam5@hotmail.com, hfun.c@ksu.edu.sa

(Received 3 June 2014; accepted 6 June 2014; online 14 June 2014)

The title compound, C₁₉H₂₃N₃S, is a functionalized triazoline-3-thione derivative. The benzyl ring is almost normal to the planar 1,2,4-triazole ring (r.m.s. deviation = 0.007 Å) with a dihedral angle of 86.90 (7)°. In the crystal, molecules are linked by pairs of N—H⋯S hydrogen bonds, forming inversion dimers that enclose R₂²(8) loops. The crystal packing is further stabilized by weak C—H⋯π interactions that link adjacent dimeric units into supramolecular chains extending along the a-axis direction.

CCDC reference: 1007119

Related literature

For the biological activity of adamantane derivatives, see: Lorenzo et al. (2008 ); Al-Deeb et al. (2006 ); Wang et al. (2013 ); El-Emam et al. (2004 ); Kadi et al. (2010 ); Balzarini et al. (2009 ); Protopopova et al. (2005 ); Vernier et al. (1969 ). For related adamantyl-1,2,4-triazole structures, see: El-Emam et al. (2012 ), Al-Tamimi et al. (2013 ). For the synthesis of the title compound, see El-Emam & Ibrahim (1991 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₂₃N₃S
M_r = 325.46
Triclinic, $[P \overline 1]$
a = 7.6407 (4) Å
b = 10.5150 (5) Å
c = 12.3434 (5) Å
α = 67.1806 (13)°
β = 72.9688 (13)°
γ = 70.0695 (14)°
V = 844.42 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.60 × 0.48 × 0.34 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.891, T_max = 0.937
43581 measured reflections
5166 independent reflections
4651 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.127
S = 1.08
5166 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1–N3/C8/C9 triazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯S1ⁱ	0.85 (2)	2.44 (2)	3.2753 (11)	169.1 (18)
C19—H19B⋯Cg1ⁱⁱ	0.97	2.85	3.7885 (17)	141
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1007119

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536814013257/sj5408sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814013257/sj5408Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814013257/sj5408Isup3.cml

checkCIF report

Comment top

Adamantane derivatives have long been known for their diverse biological activities (Lorenzo et al., 2008; Al-Deeb et al., 2006; Wang et al., 2013). These also include antiviral activity against influenza (Vernier et al., 1969) and HIV viruses (El-Emam et al., 2004; Balzarini et al., 2009). In addition, adamantane derivative were recently reported to exhibit marked antibacterial activity (Kadi et al., 2010; Protopopova et al., 2005). In an earlier publication, we reported the synthesis and potent anti-inflammatory of a series of 5-(1-adamantyl)-4-substituted-4H-1,2,4-triazole-3-thiols and related derivatives including the title compound (El-Emam & Ibrahim, 1991).

In the title compound (Fig. 1), the 1,2,4-triazole (N1—N3/C8/C9) ring is nearly planar with a maximum deviation of -0.007 (1) Å at atom N2. The central 1,2,4-triazole ring forms dihedral angles of 86.90 (7)° and 69 (4)° with the adjacent phenyl (C1–C6) and adamantyl (C10–C19) substituents attached at the 4- and 5-positions, respectively. The attached phenyl ring is almost perpendicular to the plane of the triazole which is evident from the C9–N1–C7–C6 torsion angle of -95.63 (12)°. In the crystal packing (Fig. 2), centrosymmetric dimeric aggregates are formed by pairs of N2—H1N2···S1 hydrogen bonds resulting in an R₂²(8) ring motif (Bernstein et al., 1995). These are connected into supramolecular chains extending along the a axis direction via weak intermolecular C–H···π(triazole) interactions (Table 1).

Related literature top

For the biological activity of adamantane derivatives, see: Lorenzo et al. (2008); Al-Deeb et al. (2006); Wang et al. (2013); El-Emam et al. (2004); Kadi et al. (2010); Balzarini et al. (2009); Protopopova et al. (2005); Vernier et al. (1969). For related adamantyl-1,2,4-triazole structures, see: El-Emam et al. (2012), Al-Tamimi et al. (2013). For the synthesis of the title compound, see El-Emam & Ibrahim (1991). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of adamantane-1-carbohydrazide (1.94 g, 0.01 mol), benzyl isothiocyanate (1.49 g, 0.01 mol), in ethanol (10 ml) was heated under reflux with stirring for one hour and the solvent was distilled off in vacuo. Aqueous sodium hydroxide solution (10%, 15 ml) was added to the residue and the mixture was heated under reflux for 2 h. then filtered hot. On cooling, the mixture was acidified with hydrochloric acid and the precipitated crude product was filtered, washed with water, dried and crystallized from aqueous ethanol to yield 2.93 g (90%) of the title compound (C₁₉H₂₃N₃S) as colorless crystals. M·P.: 241–243 °C.

¹H NMR (CDCl₃, 700.17 MHz): δ 1.64–1.69 (m, 6H, Adamantane-H), 1.90 (s, 6H, Adamantane-H), 2.20 (s, 3H, Adamantane-H), 5.53 (s, 2H, CH₂), 7.04–7.63 (s, 5H, Ar—H), 11.55 (br. s, 1H, NH). ¹³C NMR (CDCl₃, 176.08 MHz): δ 28.51, 35.66, 36.86, 39.08 (Adamantane-C), 63.56 (CH₂), 121.25, 123.0, 124.27, 130.54 (Ar—C), 154.06 (C=N), 164.41 (C=S).

Structure description top

For the biological activity of adamantane derivatives, see: Lorenzo et al. (2008); Al-Deeb et al. (2006); Wang et al. (2013); El-Emam et al. (2004); Kadi et al. (2010); Balzarini et al. (2009); Protopopova et al. (2005); Vernier et al. (1969). For related adamantyl-1,2,4-triazole structures, see: El-Emam et al. (2012), Al-Tamimi et al. (2013). For the synthesis of the title compound, see El-Emam & Ibrahim (1991). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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 atom labels and 50% probability displacement ellipsoids.
	Fig. 2. Crystal packing of the title compound, showing the hydrogen bonding interactions as dashed lines. H-atoms not involved in the hydrogen bonding are omitted for clarity.

3-(Adamantan-1-yl)-4-benzyl-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₁₉H₂₃N₃S	Z = 2
M_r = 325.46	F(000) = 348
Triclinic, P1	D_x = 1.280 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6407 (4) Å	Cell parameters from 9608 reflections
b = 10.5150 (5) Å	θ = 2.9–30.6°
c = 12.3434 (5) Å	µ = 0.20 mm⁻¹
α = 67.1806 (13)°	T = 293 K
β = 72.9688 (13)°	Block, colourless
γ = 70.0695 (14)°	0.60 × 0.48 × 0.34 mm
V = 844.42 (7) Å³

Data collection top

Bruker APEXII CCD diffractometer	5166 independent reflections
Radiation source: fine-focus sealed tube	4651 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 30.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.891, T_max = 0.937	k = −15→15
43581 measured reflections	l = −17→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0747P)² + 0.1424P] where P = (F_o² + 2F_c²)/3
5166 reflections	(Δ/σ)_max = 0.001
212 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₉H₂₃N₃S	γ = 70.0695 (14)°
M_r = 325.46	V = 844.42 (7) Å³
Triclinic, P1	Z = 2
a = 7.6407 (4) Å	Mo Kα radiation
b = 10.5150 (5) Å	µ = 0.20 mm⁻¹
c = 12.3434 (5) Å	T = 293 K
α = 67.1806 (13)°	0.60 × 0.48 × 0.34 mm
β = 72.9688 (13)°

Data collection top

Bruker APEXII CCD diffractometer	5166 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4651 reflections with I > 2σ(I)
T_min = 0.891, T_max = 0.937	R_int = 0.029
43581 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.31 e Å⁻³
5166 reflections	Δρ_min = −0.56 e Å⁻³
212 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	1.05370 (4)	0.44991 (3)	0.32578 (3)	0.03965 (10)
N1	0.70863 (12)	0.63160 (9)	0.28216 (7)	0.02792 (16)
N2	0.74865 (14)	0.58334 (11)	0.45903 (8)	0.0360 (2)
N3	0.57266 (14)	0.67716 (11)	0.45231 (8)	0.0359 (2)
C1	0.75626 (15)	0.49115 (13)	0.03402 (10)	0.0363 (2)
H1A	0.8142	0.5555	−0.0302	0.044*
C2	0.71844 (19)	0.38114 (15)	0.01658 (13)	0.0471 (3)
H2A	0.7512	0.3719	−0.0593	0.057*
C3	0.6325 (2)	0.28550 (15)	0.11137 (15)	0.0522 (3)
H3A	0.6073	0.2118	0.0995	0.063*
C4	0.5840 (2)	0.29922 (14)	0.22381 (14)	0.0497 (3)
H4A	0.5253	0.2349	0.2876	0.060*
C5	0.62220 (17)	0.40876 (12)	0.24249 (10)	0.0390 (2)
H5A	0.5903	0.4169	0.3187	0.047*
C6	0.70774 (13)	0.50549 (10)	0.14754 (8)	0.02895 (19)
C7	0.75127 (15)	0.62875 (11)	0.15983 (8)	0.03048 (19)
H7A	0.8846	0.6242	0.1282	0.037*
H7B	0.6793	0.7175	0.1113	0.037*
C8	0.83679 (14)	0.55430 (10)	0.35740 (9)	0.03030 (19)
C9	0.54907 (13)	0.70511 (10)	0.34398 (8)	0.02803 (18)
C10	0.37568 (13)	0.81094 (10)	0.29687 (8)	0.02757 (18)
C11	0.22454 (18)	0.84649 (16)	0.40233 (11)	0.0460 (3)
H11A	0.1894	0.7604	0.4584	0.055*
H11B	0.2761	0.8830	0.4439	0.055*
C12	0.04846 (19)	0.95844 (17)	0.35680 (13)	0.0513 (3)
H12A	−0.0461	0.9806	0.4247	0.062*
C13	0.1044 (2)	1.09463 (16)	0.26935 (19)	0.0642 (4)
H13A	0.1566	1.1326	0.3094	0.077*
H13B	−0.0065	1.1663	0.2411	0.077*
C14	0.2523 (2)	1.05937 (13)	0.16312 (15)	0.0553 (4)
H14A	0.2873	1.1465	0.1064	0.066*
C15	0.1686 (2)	0.99973 (17)	0.10091 (13)	0.0546 (3)
H15A	0.0585	1.0705	0.0709	0.065*
H15B	0.2614	0.9773	0.0336	0.065*
C16	0.11210 (18)	0.86562 (14)	0.18917 (12)	0.0436 (3)
H16A	0.0581	0.8279	0.1488	0.052*
C17	0.28778 (16)	0.75284 (12)	0.23410 (11)	0.0380 (2)
H17A	0.3800	0.7290	0.1672	0.046*
H17B	0.2524	0.6667	0.2897	0.046*
C18	0.42886 (18)	0.94874 (12)	0.20848 (12)	0.0428 (3)
H18A	0.4818	0.9870	0.2479	0.051*
H18B	0.5239	0.9277	0.1415	0.051*
C19	−0.03504 (18)	0.90065 (16)	0.29388 (14)	0.0499 (3)
H19A	−0.1464	0.9712	0.2654	0.060*
H19B	−0.0728	0.8153	0.3493	0.060*
H1N2	0.798 (3)	0.5628 (19)	0.5188 (16)	0.056 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03414 (15)	0.04240 (16)	0.04517 (17)	0.00090 (11)	−0.01292 (11)	−0.02211 (12)
N1	0.0301 (4)	0.0295 (4)	0.0249 (3)	−0.0049 (3)	−0.0058 (3)	−0.0114 (3)
N2	0.0363 (4)	0.0423 (5)	0.0276 (4)	−0.0032 (4)	−0.0107 (3)	−0.0118 (3)
N3	0.0351 (4)	0.0435 (5)	0.0264 (4)	−0.0027 (4)	−0.0068 (3)	−0.0140 (3)
C1	0.0341 (5)	0.0463 (6)	0.0330 (5)	−0.0067 (4)	−0.0059 (4)	−0.0208 (4)
C2	0.0439 (6)	0.0582 (7)	0.0537 (7)	−0.0057 (5)	−0.0127 (5)	−0.0368 (6)
C3	0.0468 (7)	0.0482 (7)	0.0780 (9)	−0.0082 (5)	−0.0187 (6)	−0.0355 (7)
C4	0.0485 (7)	0.0399 (6)	0.0619 (8)	−0.0167 (5)	−0.0066 (6)	−0.0158 (5)
C5	0.0414 (6)	0.0381 (5)	0.0367 (5)	−0.0109 (4)	−0.0020 (4)	−0.0144 (4)
C6	0.0261 (4)	0.0323 (4)	0.0295 (4)	−0.0029 (3)	−0.0052 (3)	−0.0149 (3)
C7	0.0348 (5)	0.0337 (5)	0.0238 (4)	−0.0092 (4)	−0.0022 (3)	−0.0122 (3)
C8	0.0327 (4)	0.0295 (4)	0.0302 (4)	−0.0067 (3)	−0.0087 (3)	−0.0103 (3)
C9	0.0301 (4)	0.0295 (4)	0.0242 (4)	−0.0063 (3)	−0.0044 (3)	−0.0101 (3)
C10	0.0292 (4)	0.0276 (4)	0.0256 (4)	−0.0053 (3)	−0.0050 (3)	−0.0101 (3)
C11	0.0372 (5)	0.0618 (7)	0.0336 (5)	0.0026 (5)	−0.0053 (4)	−0.0240 (5)
C12	0.0377 (6)	0.0647 (8)	0.0516 (7)	0.0076 (5)	−0.0096 (5)	−0.0357 (6)
C13	0.0572 (8)	0.0428 (7)	0.1067 (13)	0.0107 (6)	−0.0372 (9)	−0.0429 (8)
C14	0.0536 (7)	0.0294 (5)	0.0729 (9)	−0.0095 (5)	−0.0244 (7)	0.0022 (5)
C15	0.0523 (7)	0.0577 (8)	0.0418 (6)	−0.0021 (6)	−0.0200 (6)	−0.0058 (6)
C16	0.0399 (6)	0.0473 (6)	0.0527 (7)	−0.0034 (5)	−0.0192 (5)	−0.0243 (5)
C17	0.0377 (5)	0.0351 (5)	0.0480 (6)	−0.0052 (4)	−0.0136 (4)	−0.0199 (4)
C18	0.0402 (6)	0.0310 (5)	0.0536 (7)	−0.0126 (4)	−0.0123 (5)	−0.0043 (4)
C19	0.0324 (5)	0.0551 (7)	0.0610 (8)	−0.0069 (5)	−0.0090 (5)	−0.0207 (6)

Geometric parameters (Å, º) top

S1—C8	1.6784 (10)	C10—C17	1.5415 (14)
N1—C8	1.3735 (12)	C11—C12	1.5368 (18)
N1—C9	1.3915 (12)	C11—H11A	0.9700
N1—C7	1.4586 (12)	C11—H11B	0.9700
N2—C8	1.3351 (13)	C12—C19	1.517 (2)
N2—N3	1.3732 (13)	C12—C13	1.532 (3)
N2—H1N2	0.846 (19)	C12—H12A	0.9800
N3—C9	1.3065 (12)	C13—C14	1.535 (3)
C1—C2	1.3876 (16)	C13—H13A	0.9700
C1—C6	1.3946 (13)	C13—H13B	0.9700
C1—H1A	0.9300	C14—C15	1.525 (2)
C2—C3	1.378 (2)	C14—C18	1.5344 (18)
C2—H2A	0.9300	C14—H14A	0.9800
C3—C4	1.379 (2)	C15—C16	1.520 (2)
C3—H3A	0.9300	C15—H15A	0.9700
C4—C5	1.3929 (17)	C15—H15B	0.9700
C4—H4A	0.9300	C16—C19	1.5185 (19)
C5—C6	1.3840 (15)	C16—C17	1.5351 (16)
C5—H5A	0.9300	C16—H16A	0.9800
C6—C7	1.5131 (13)	C17—H17A	0.9700
C7—H7A	0.9700	C17—H17B	0.9700
C7—H7B	0.9700	C18—H18A	0.9700
C9—C10	1.5086 (13)	C18—H18B	0.9700
C10—C11	1.5396 (14)	C19—H19A	0.9700
C10—C18	1.5396 (14)	C19—H19B	0.9700

C8—N1—C9	108.06 (8)	C19—C12—C13	109.53 (12)
C8—N1—C7	121.22 (8)	C19—C12—C11	109.84 (11)
C9—N1—C7	130.71 (8)	C13—C12—C11	109.41 (12)
C8—N2—N3	113.41 (9)	C19—C12—H12A	109.3
C8—N2—H1N2	126.3 (12)	C13—C12—H12A	109.3
N3—N2—H1N2	119.1 (12)	C11—C12—H12A	109.3
C9—N3—N2	104.79 (8)	C12—C13—C14	109.13 (10)
C2—C1—C6	120.22 (11)	C12—C13—H13A	109.9
C2—C1—H1A	119.9	C14—C13—H13A	109.9
C6—C1—H1A	119.9	C12—C13—H13B	109.9
C3—C2—C1	120.15 (11)	C14—C13—H13B	109.9
C3—C2—H2A	119.9	H13A—C13—H13B	108.3
C1—C2—H2A	119.9	C15—C14—C18	109.88 (12)
C2—C3—C4	119.91 (11)	C15—C14—C13	109.38 (12)
C2—C3—H3A	120.0	C18—C14—C13	109.37 (13)
C4—C3—H3A	120.0	C15—C14—H14A	109.4
C3—C4—C5	120.43 (12)	C18—C14—H14A	109.4
C3—C4—H4A	119.8	C13—C14—H14A	109.4
C5—C4—H4A	119.8	C16—C15—C14	109.44 (11)
C6—C5—C4	119.92 (11)	C16—C15—H15A	109.8
C6—C5—H5A	120.0	C14—C15—H15A	109.8
C4—C5—H5A	120.0	C16—C15—H15B	109.8
C5—C6—C1	119.36 (10)	C14—C15—H15B	109.8
C5—C6—C7	123.23 (9)	H15A—C15—H15B	108.2
C1—C6—C7	117.40 (9)	C19—C16—C15	109.94 (11)
N1—C7—C6	114.42 (8)	C19—C16—C17	109.96 (11)
N1—C7—H7A	108.7	C15—C16—C17	109.53 (10)
C6—C7—H7A	108.7	C19—C16—H16A	109.1
N1—C7—H7B	108.7	C15—C16—H16A	109.1
C6—C7—H7B	108.7	C17—C16—H16A	109.1
H7A—C7—H7B	107.6	C16—C17—C10	109.85 (9)
N2—C8—N1	103.79 (9)	C16—C17—H17A	109.7
N2—C8—S1	129.01 (8)	C10—C17—H17A	109.7
N1—C8—S1	127.19 (8)	C16—C17—H17B	109.7
N3—C9—N1	109.93 (9)	C10—C17—H17B	109.7
N3—C9—C10	122.14 (9)	H17A—C17—H17B	108.2
N1—C9—C10	127.80 (8)	C14—C18—C10	109.81 (9)
C9—C10—C11	108.87 (8)	C14—C18—H18A	109.7
C9—C10—C18	109.22 (8)	C10—C18—H18A	109.7
C11—C10—C18	108.93 (10)	C14—C18—H18B	109.7
C9—C10—C17	112.77 (8)	C10—C18—H18B	109.7
C11—C10—C17	107.69 (9)	H18A—C18—H18B	108.2
C18—C10—C17	109.28 (9)	C12—C19—C16	109.24 (10)
C12—C11—C10	110.21 (10)	C12—C19—H19A	109.8
C12—C11—H11A	109.6	C16—C19—H19A	109.8
C10—C11—H11A	109.6	C12—C19—H19B	109.8
C12—C11—H11B	109.6	C16—C19—H19B	109.8
C10—C11—H11B	109.6	H19A—C19—H19B	108.3
H11A—C11—H11B	108.1

C8—N2—N3—C9	1.25 (13)	N3—C9—C10—C17	−132.65 (10)
C6—C1—C2—C3	0.06 (19)	N1—C9—C10—C17	51.96 (13)
C1—C2—C3—C4	0.0 (2)	C9—C10—C11—C12	177.91 (10)
C2—C3—C4—C5	−0.4 (2)	C18—C10—C11—C12	58.90 (14)
C3—C4—C5—C6	0.7 (2)	C17—C10—C11—C12	−59.52 (13)
C4—C5—C6—C1	−0.56 (17)	C10—C11—C12—C19	60.43 (15)
C4—C5—C6—C7	179.01 (11)	C10—C11—C12—C13	−59.83 (15)
C2—C1—C6—C5	0.21 (16)	C19—C12—C13—C14	−60.12 (15)
C2—C1—C6—C7	−179.39 (10)	C11—C12—C13—C14	60.33 (15)
C8—N1—C7—C6	85.08 (11)	C12—C13—C14—C15	59.48 (15)
C9—N1—C7—C6	−95.63 (12)	C12—C13—C14—C18	−60.91 (15)
C5—C6—C7—N1	4.38 (14)	C18—C14—C15—C16	60.57 (16)
C1—C6—C7—N1	−176.04 (9)	C13—C14—C15—C16	−59.51 (15)
N3—N2—C8—N1	−1.21 (12)	C14—C15—C16—C19	60.18 (14)
N3—N2—C8—S1	178.19 (8)	C14—C15—C16—C17	−60.75 (14)
C9—N1—C8—N2	0.70 (11)	C19—C16—C17—C10	−60.82 (13)
C7—N1—C8—N2	−179.87 (9)	C15—C16—C17—C10	60.09 (13)
C9—N1—C8—S1	−178.72 (7)	C9—C10—C17—C16	179.74 (9)
C7—N1—C8—S1	0.71 (14)	C11—C10—C17—C16	59.61 (12)
N2—N3—C9—N1	−0.74 (11)	C18—C10—C17—C16	−58.58 (12)
N2—N3—C9—C10	−176.86 (9)	C15—C14—C18—C10	−59.41 (15)
C8—N1—C9—N3	0.04 (11)	C13—C14—C18—C10	60.67 (14)
C7—N1—C9—N3	−179.32 (10)	C9—C10—C18—C14	−178.04 (10)
C8—N1—C9—C10	175.88 (9)	C11—C10—C18—C14	−59.25 (14)
C7—N1—C9—C10	−3.48 (16)	C17—C10—C18—C14	58.16 (13)
N3—C9—C10—C11	−13.20 (14)	C13—C12—C19—C16	60.51 (14)
N1—C9—C10—C11	171.41 (10)	C11—C12—C19—C16	−59.68 (15)
N3—C9—C10—C18	105.64 (11)	C15—C16—C19—C12	−60.60 (14)
N1—C9—C10—C18	−69.75 (12)	C17—C16—C19—C12	60.06 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1–N3/C8/C9 triazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1ⁱ	0.85 (2)	2.44 (2)	3.2753 (11)	169.1 (18)
C19—H19B···Cg1ⁱⁱ	0.97	2.85	3.7885 (17)	141

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1–N3/C8/C9 triazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1ⁱ	0.85 (2)	2.44 (2)	3.2753 (11)	169.1 (18)
C19—H19B···Cg1ⁱⁱ	0.9700	2.85	3.7885 (17)	141

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

Footnotes

‡Thomson Reuters ResearcherID: C-3194-2011.

§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

Al-Deeb, O. A., Al-Omar, M. A., El-Brollosy, N. R., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2006). Arzneim. Forsch. Drug. Res. 56, 40–47. CAS Google Scholar
Al-Tamimi, A.-M. S., Al-Abdullah, E. S., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o685–o686. CSD CrossRef CAS IUCr Journals Google Scholar
Balzarini, J., Orzeszko-Krzesinska, B., Maurin, J. K. & Orzeszko, A. (2009). Eur. J. Med. Chem. 44, 303–311. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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
El-Emam, A. A., El-Brollosy, N. R., Ghabbour, H. A., Quah, C. K. & Fun, H.-K. (2012). Acta Cryst. E68, o1347. CSD CrossRef IUCr Journals Google Scholar
El-Emam, A. A. & Ibrahim, T. M. (1991). Arzneim. Forsch. Drug. Res. 41, 1260–1264. CAS 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
Lorenzo, P., Alvarez, R., Ortiz, M. A., Alvarez, S., Piedrafita, F. J. & de Lera, A. (2008). J. Med. Chem. 51, 5431–5440. Web of Science CrossRef PubMed CAS Google Scholar
Protopopova, M., Hanrahan, C., Nikonenko, B., Samala, R., Chen, P., Gearhart, J., Einck, L. & Nacy, C. A. (2005). J. Antimicrob. Chemother. 56, 968–974. 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. 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
Wang, J., Ma, C., Wang, J., Jo, H., Canturk, B., Fiorin, G., Pinto, L. H., Lamb, R. A., Klein, M. L. & DeGrado, W. F. (2013). J. Med. Chem. 56, 2804–2812. Web of Science CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 7| July 2014| Pages o766-o767

https://doi.org/10.1107/S1600536814013257

Open

access