N-(4-Bromo­phen­yl)-2-[(1-cyclo­hexyl­meth­yl-1H-1,2,4-triazol-3-yl)sulfanyl]­acetamide

Wang, Y.-P.; Yan, W.-L.; Guo, Q.; He, Y.-P.

doi:10.1107/S1600536812015991

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1495

doi:10.1107/S1600536812015991

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N-(4-Bromophenyl)-2-[(1-cyclohexylmethyl-1H-1,2,4-triazol-3-yl)sulfanyl]acetamide

Yue-Ping Wang,^a Wan-Lu Yan,^b ^* Qiong Guo ^b and Yan-Ping He ^b

^aDepartment of Applied Chemistry, Faculty of Science, Kunming University of Science and Technology, Kunming, 650050, People's Republic of China, and ^bKey Laboratory of Medicinal Chemistry for Natural Resource, (Ministry of Education), School of Chemical Science and Technology, Yunnan University, Kunming 650091, People's Republic of China
^*Correspondence e-mail: yphe@ynu.edu.cn

(Received 5 April 2012; accepted 12 April 2012; online 21 April 2012)

The title compound, C₁₇H₂₁BrN₄OS, was synthesized as a potential reverse transcriptase (RT) inhibitor of the human immunodeficiency virus type 1 (HIV-1). In the molecule, there is an N—H⋯S hydrogen bond making a five-membered ring. In the crystal, molecules are connected into centrosymmetric dimers via pairs of N—H⋯N and weak C—H⋯N hydrogen bonds. The crystal structure also features C—H⋯O interactions.

Related literature

The 1,2,4-triazole scaffold and its analogues are important pharmacophores that can be found in biologically active compounds across a number of different therapeutic areas, see: Lin et al. (2005 ); Naito et al. (1996 ); Sui et al. (1998 ); Tafi et al. (2002 ).

Experimental

Crystal data

C₁₇H₂₁BrN₄OS
M_r = 409.35
Triclinic, $[P \overline 1]$
a = 7.2061 (8) Å
b = 9.521 (1) Å
c = 14.2862 (16) Å
α = 104.132 (1)°
β = 90.804 (1)°
γ = 95.820 (1)°
V = 944.84 (18) Å³
Z = 2
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 298 K
0.25 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.597, T_max = 0.770
8793 measured reflections
4076 independent reflections
2644 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.092
S = 1.01
4076 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯S1	0.86	2.61	3.096 (2)	117
N4—H4⋯N1ⁱ	0.86	2.55	3.339 (3)	153
C1—H1⋯O1ⁱⁱ	0.93	2.29	3.214 (3)	171
C13—H13⋯N1ⁱ	0.93	2.48	3.342 (3)	153
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x, y+1, z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812015991/bq2348sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015991/bq2348Isup2.hkl

checkCIF report

Comment top

The 1,2,4-triazole scaffold and its analogues are important pharmacophores that can be found in biologically active compounds across a number of different therapeutic areas; these include antifungal (Tafi, et al., 2002), antibacterial (Sui, et al., 1998), antiasthmatic (Naito, et al., 1996) and anticancer activities (Lin, et al., 2005), etc. In the course of our search for new anti-HIV-1 agents, we have synthesized a new series of 1,2,4-triazole analogues, including the title compound, (I), as potential HIV-1 inhibitors.

The chemical structure of (I) is shown in Fig.1. The molecule is stabilized by a weak intramolecular N4—H4···S1 hydrogen bond (Table 1). The cyclohexyl ring adopts the lowest energy chair conformation. The torsion angle (C1—N3—C2—C3), which describes the arrangement between the cyclohexyl ring and the triazole moiety, is -112.1 (3) °; the torsion angle C12—N4—C11—O1, which characterizes the location of the CONH₂ group relative to the phenyl ring, is 3.5 (4) °.

In the crystal structure, centrosymmetric dimmers are formed by pairs of N4—H4···N1ⁱ and C13—H13···N1ⁱ hydrogen bonds [symmetry code: (i) -x + 1, -y + 2,-z + 1]. These dimmers are further linked into chains by weak C—H···O interactions (Table 1, Fig.2).

Related literature top

The 1,2,4-triazole scaffold and its analogues are important pharmacophores that can be found in biologically active compounds across a number of different therapeutic areas, see: Lin et al. (2005); Naito et al. (1996); Sui et al. (1998); Tafi et al. (2002).

Experimental top

To a stirred solution of 2-((1H-1,2,4-triazol-3-yl)thio)-N-(4-bromophenyl)acetamide (3.12 g, 10 mmol) in anhydrous EtOH (75 ml) was added K₂CO₃ (1.38 g, 0.01 mol) under a nitrogen atmosphere. The mixture was stirred at 298 K for 15 min, then (bromomethyl)cyclohexane (0.53 g, 0.03 mol) was added, and the reaction mixture was refluxed for 8 h under a nitrogen atmosphere. The reaction mixture was poured into cold H₂O (80 ml), then the aqueous phase was extracted with EtOAc (3×50 ml). The combined organic layer was washed with H₂O (3×50 ml), dried (Mg₂SO₄), filtered and concentrated in vacuo to give the crude product, which was purified by chromatography (eluent EtOAc/PE 100:25) to afford the title compound (yield: 23%; m.p. 398.7–398.9 K). Single crystals of (I) suitable for X-ray diffraction were grown from a solution in EtOAc by slow evaporation. The product was characterized by IR, MS, ¹H NMR and ¹³C NMR.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom labeling scheme and 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. Intermolecular N—H···Nⁱ, C—H···Nⁱ, C—H···Oⁱⁱ hydrogen bond are shown as dashed lines [symmetry codes: (i) -x + 1, -y + 2, -z + 1; (ii) x, 1 + y, z].

N-(4-Bromophenyl)-2-[(1-cyclohexylmethyl-1H-1,2,4-triazol- 3-yl)sulfanyl]acetamide top

Crystal data top

C₁₇H₂₁BrN₄OS	Z = 2
M_r = 409.35	F(000) = 420
Triclinic, P1	D_x = 1.439 Mg m⁻³
Hall symbol: -P 1	Melting point: 398.8(1) K
a = 7.2061 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.521 (1) Å	Cell parameters from 2212 reflections
c = 14.2862 (16) Å	θ = 2.3–24.5°
α = 104.132 (1)°	µ = 2.30 mm⁻¹
β = 90.804 (1)°	T = 298 K
γ = 95.820 (1)°	Block, colourless
V = 944.84 (18) Å³	0.25 × 0.16 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4076 independent reflections
Radiation source: fine-focus sealed tube	2644 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
phi and ω scans	θ_max = 27.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→8
T_min = 0.597, T_max = 0.770	k = −12→12
8793 measured reflections	l = −18→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0382P)² + 0.1448P] where P = (F_o² + 2F_c²)/3
4076 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₇H₂₁BrN₄OS	γ = 95.820 (1)°
M_r = 409.35	V = 944.84 (18) Å³
Triclinic, P1	Z = 2
a = 7.2061 (8) Å	Mo Kα radiation
b = 9.521 (1) Å	µ = 2.30 mm⁻¹
c = 14.2862 (16) Å	T = 298 K
α = 104.132 (1)°	0.25 × 0.16 × 0.12 mm
β = 90.804 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4076 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2644 reflections with I > 2σ(I)
T_min = 0.597, T_max = 0.770	R_int = 0.025
8793 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.01	Δρ_max = 0.34 e Å⁻³
4076 reflections	Δρ_min = −0.42 e Å⁻³
217 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
Br1	1.07267 (5)	0.57798 (4)	0.86425 (2)	0.07787 (16)
N1	0.2679 (3)	1.0737 (2)	0.49703 (17)	0.0506 (6)
N2	0.1739 (3)	0.9382 (2)	0.60131 (15)	0.0444 (5)
N3	0.1580 (3)	1.0832 (2)	0.64012 (16)	0.0461 (5)
N4	0.4730 (3)	0.6839 (2)	0.59376 (15)	0.0434 (5)
H4	0.5020	0.7572	0.5696	0.052*
O1	0.2434 (3)	0.5032 (2)	0.59473 (15)	0.0683 (6)
S1	0.28308 (9)	0.78377 (7)	0.42896 (5)	0.04868 (18)
C1	0.2140 (4)	1.1586 (3)	0.5772 (2)	0.0532 (7)
H1	0.2151	1.2590	0.5881	0.064*
C2	0.0908 (4)	1.1312 (3)	0.7364 (2)	0.0557 (7)
H2A	−0.0288	1.0766	0.7404	0.067*
H2B	0.0714	1.2333	0.7483	0.067*
C3	0.2247 (4)	1.1117 (3)	0.81422 (19)	0.0537 (7)
H3	0.2486	1.0092	0.7988	0.064*
C4	0.4098 (4)	1.2034 (4)	0.8179 (2)	0.0726 (9)
H4A	0.3883	1.3049	0.8277	0.087*
H4B	0.4685	1.1743	0.7565	0.087*
C5	0.5408 (5)	1.1879 (5)	0.8986 (3)	0.0958 (12)
H5A	0.5750	1.0892	0.8847	0.115*
H5B	0.6540	1.2537	0.9016	0.115*
C6	0.4501 (7)	1.2220 (5)	0.9949 (3)	0.1066 (14)
H6A	0.5329	1.2047	1.0440	0.128*
H6B	0.4294	1.3241	1.0124	0.128*
C7	0.2675 (6)	1.1298 (5)	0.9914 (2)	0.0935 (12)
H7A	0.2096	1.1578	1.0531	0.112*
H7B	0.2901	1.0285	0.9808	0.112*
C8	0.1356 (5)	1.1455 (4)	0.9123 (2)	0.0755 (9)
H8A	0.1012	1.2442	0.9268	0.091*
H8B	0.0227	1.0797	0.9098	0.091*
C9	0.2392 (3)	0.9403 (3)	0.51580 (18)	0.0405 (6)
C10	0.1917 (4)	0.6457 (3)	0.48677 (19)	0.0465 (6)
H10A	0.0761	0.6752	0.5154	0.056*
H10B	0.1590	0.5573	0.4363	0.056*
C11	0.3064 (4)	0.6054 (3)	0.56361 (19)	0.0435 (6)
C12	0.6046 (3)	0.6588 (2)	0.66041 (17)	0.0397 (6)
C13	0.7805 (3)	0.7356 (3)	0.66796 (18)	0.0449 (6)
H13	0.8052	0.8042	0.6320	0.054*
C14	0.9196 (4)	0.7118 (3)	0.72794 (19)	0.0494 (6)
H14	1.0376	0.7631	0.7319	0.059*
C15	0.8817 (4)	0.6118 (3)	0.78159 (18)	0.0487 (6)
C16	0.7086 (4)	0.5367 (3)	0.7767 (2)	0.0575 (7)
H16	0.6845	0.4700	0.8141	0.069*
C17	0.5691 (4)	0.5594 (3)	0.71644 (19)	0.0548 (7)
H17	0.4513	0.5082	0.7134	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0771 (3)	0.0900 (3)	0.0738 (2)	0.01971 (19)	−0.02021 (18)	0.03131 (19)
N1	0.0502 (13)	0.0471 (13)	0.0616 (15)	−0.0016 (11)	−0.0049 (11)	0.0299 (12)
N2	0.0453 (12)	0.0378 (12)	0.0519 (13)	0.0023 (10)	−0.0001 (10)	0.0156 (10)
N3	0.0460 (13)	0.0382 (12)	0.0539 (14)	0.0033 (10)	−0.0043 (10)	0.0119 (10)
N4	0.0402 (12)	0.0394 (11)	0.0550 (13)	0.0011 (10)	−0.0018 (10)	0.0217 (10)
O1	0.0601 (13)	0.0535 (12)	0.0978 (16)	−0.0140 (10)	−0.0139 (11)	0.0406 (12)
S1	0.0452 (4)	0.0554 (4)	0.0474 (4)	0.0041 (3)	0.0001 (3)	0.0172 (3)
C1	0.0509 (16)	0.0387 (15)	0.074 (2)	0.0001 (13)	−0.0130 (15)	0.0247 (15)
C2	0.0510 (17)	0.0502 (16)	0.0640 (19)	0.0086 (13)	0.0011 (14)	0.0091 (14)
C3	0.0556 (17)	0.0485 (16)	0.0580 (17)	0.0070 (13)	0.0034 (14)	0.0145 (13)
C4	0.060 (2)	0.087 (2)	0.074 (2)	−0.0060 (18)	−0.0076 (16)	0.0336 (18)
C5	0.070 (2)	0.128 (3)	0.098 (3)	−0.007 (2)	−0.025 (2)	0.051 (3)
C6	0.123 (4)	0.119 (3)	0.076 (3)	0.001 (3)	−0.031 (3)	0.026 (2)
C7	0.126 (4)	0.105 (3)	0.056 (2)	0.026 (3)	0.008 (2)	0.027 (2)
C8	0.083 (2)	0.078 (2)	0.066 (2)	0.0134 (19)	0.0163 (19)	0.0176 (18)
C9	0.0322 (13)	0.0427 (14)	0.0492 (15)	−0.0013 (11)	−0.0073 (11)	0.0191 (12)
C10	0.0425 (15)	0.0378 (14)	0.0566 (16)	−0.0001 (11)	−0.0033 (12)	0.0087 (12)
C11	0.0409 (15)	0.0342 (13)	0.0544 (16)	0.0046 (11)	0.0007 (12)	0.0086 (12)
C12	0.0415 (14)	0.0355 (13)	0.0446 (14)	0.0055 (11)	0.0020 (11)	0.0141 (11)
C13	0.0465 (15)	0.0410 (14)	0.0498 (15)	−0.0022 (12)	−0.0011 (12)	0.0192 (12)
C14	0.0428 (15)	0.0464 (15)	0.0581 (17)	−0.0043 (12)	−0.0051 (13)	0.0153 (13)
C15	0.0555 (17)	0.0498 (16)	0.0436 (15)	0.0113 (14)	−0.0053 (12)	0.0149 (12)
C16	0.0617 (19)	0.0613 (18)	0.0582 (18)	−0.0004 (15)	0.0003 (15)	0.0343 (15)
C17	0.0482 (16)	0.0591 (17)	0.0623 (18)	−0.0054 (14)	0.0002 (14)	0.0298 (15)

Geometric parameters (Å, º) top

Br1—C15	1.903 (2)	C5—H5A	0.9700
N1—C1	1.319 (3)	C5—H5B	0.9700
N1—C9	1.357 (3)	C6—C7	1.499 (5)
N2—C9	1.319 (3)	C6—H6A	0.9700
N2—N3	1.373 (3)	C6—H6B	0.9700
N3—C1	1.324 (3)	C7—C8	1.512 (5)
N3—C2	1.447 (3)	C7—H7A	0.9700
N4—C11	1.353 (3)	C7—H7B	0.9700
N4—C12	1.412 (3)	C8—H8A	0.9700
N4—H4	0.8600	C8—H8B	0.9700
O1—C11	1.215 (3)	C10—C11	1.510 (3)
S1—C9	1.750 (3)	C10—H10A	0.9700
S1—C10	1.793 (3)	C10—H10B	0.9700
C1—H1	0.9300	C12—C13	1.387 (3)
C2—C3	1.519 (4)	C12—C17	1.388 (3)
C2—H2A	0.9700	C13—C14	1.381 (3)
C2—H2B	0.9700	C13—H13	0.9300
C3—C4	1.512 (4)	C14—C15	1.371 (4)
C3—C8	1.525 (4)	C14—H14	0.9300
C3—H3	0.9800	C15—C16	1.365 (4)
C4—C5	1.525 (4)	C16—C17	1.382 (4)
C4—H4A	0.9700	C16—H16	0.9300
C4—H4B	0.9700	C17—H17	0.9300
C5—C6	1.508 (5)

C1—N1—C9	101.8 (2)	C6—C7—C8	112.0 (3)
C9—N2—N3	101.66 (19)	C6—C7—H7A	109.2
C1—N3—N2	109.2 (2)	C8—C7—H7A	109.2
C1—N3—C2	130.5 (2)	C6—C7—H7B	109.2
N2—N3—C2	120.3 (2)	C8—C7—H7B	109.2
C11—N4—C12	127.3 (2)	H7A—C7—H7B	107.9
C11—N4—H4	116.4	C7—C8—C3	111.3 (3)
C12—N4—H4	116.4	C7—C8—H8A	109.4
C9—S1—C10	100.22 (12)	C3—C8—H8A	109.4
N1—C1—N3	111.7 (2)	C7—C8—H8B	109.4
N1—C1—H1	124.1	C3—C8—H8B	109.4
N3—C1—H1	124.1	H8A—C8—H8B	108.0
N3—C2—C3	112.8 (2)	N2—C9—N1	115.6 (2)
N3—C2—H2A	109.0	N2—C9—S1	123.67 (18)
C3—C2—H2A	109.0	N1—C9—S1	120.7 (2)
N3—C2—H2B	109.0	C11—C10—S1	120.69 (18)
C3—C2—H2B	109.0	C11—C10—H10A	107.2
H2A—C2—H2B	107.8	S1—C10—H10A	107.2
C4—C3—C2	112.2 (2)	C11—C10—H10B	107.2
C4—C3—C8	110.8 (3)	S1—C10—H10B	107.2
C2—C3—C8	110.2 (2)	H10A—C10—H10B	106.8
C4—C3—H3	107.8	O1—C11—N4	123.6 (2)
C2—C3—H3	107.8	O1—C11—C10	117.7 (2)
C8—C3—H3	107.8	N4—C11—C10	118.6 (2)
C3—C4—C5	111.9 (3)	C13—C12—C17	118.6 (2)
C3—C4—H4A	109.2	C13—C12—N4	117.6 (2)
C5—C4—H4A	109.2	C17—C12—N4	123.8 (2)
C3—C4—H4B	109.2	C14—C13—C12	121.1 (2)
C5—C4—H4B	109.2	C14—C13—H13	119.5
H4A—C4—H4B	107.9	C12—C13—H13	119.5
C6—C5—C4	111.2 (3)	C15—C14—C13	119.2 (2)
C6—C5—H5A	109.4	C15—C14—H14	120.4
C4—C5—H5A	109.4	C13—C14—H14	120.4
C6—C5—H5B	109.4	C16—C15—C14	120.8 (2)
C4—C5—H5B	109.4	C16—C15—Br1	119.7 (2)
H5A—C5—H5B	108.0	C14—C15—Br1	119.5 (2)
C7—C6—C5	111.2 (3)	C15—C16—C17	120.3 (2)
C7—C6—H6A	109.4	C15—C16—H16	119.9
C5—C6—H6A	109.4	C17—C16—H16	119.9
C7—C6—H6B	109.4	C16—C17—C12	120.0 (3)
C5—C6—H6B	109.4	C16—C17—H17	120.0
H6A—C6—H6B	108.0	C12—C17—H17	120.0

C9—N2—N3—C1	−0.3 (3)	C1—N1—C9—S1	178.04 (18)
C9—N2—N3—C2	−179.5 (2)	C10—S1—C9—N2	6.0 (2)
C9—N1—C1—N3	0.4 (3)	C10—S1—C9—N1	−172.49 (19)
N2—N3—C1—N1	−0.1 (3)	C9—S1—C10—C11	−81.3 (2)
C2—N3—C1—N1	179.1 (2)	C12—N4—C11—O1	3.5 (4)
C1—N3—C2—C3	−112.1 (3)	C12—N4—C11—C10	−176.2 (2)
N2—N3—C2—C3	67.0 (3)	S1—C10—C11—O1	−174.2 (2)
N3—C2—C3—C4	63.3 (3)	S1—C10—C11—N4	5.5 (3)
N3—C2—C3—C8	−172.7 (2)	C11—N4—C12—C13	168.5 (2)
C2—C3—C4—C5	177.8 (3)	C11—N4—C12—C17	−9.8 (4)
C8—C3—C4—C5	54.1 (4)	C17—C12—C13—C14	1.6 (4)
C3—C4—C5—C6	−54.9 (4)	N4—C12—C13—C14	−176.8 (2)
C4—C5—C6—C7	55.1 (5)	C12—C13—C14—C15	−0.8 (4)
C5—C6—C7—C8	−55.9 (5)	C13—C14—C15—C16	−0.4 (4)
C6—C7—C8—C3	55.4 (4)	C13—C14—C15—Br1	179.86 (19)
C4—C3—C8—C7	−54.1 (4)	C14—C15—C16—C17	0.7 (4)
C2—C3—C8—C7	−178.8 (3)	Br1—C15—C16—C17	−179.5 (2)
N3—N2—C9—N1	0.5 (3)	C15—C16—C17—C12	0.1 (4)
N3—N2—C9—S1	−178.05 (16)	C13—C12—C17—C16	−1.3 (4)
C1—N1—C9—N2	−0.6 (3)	N4—C12—C17—C16	177.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···S1	0.86	2.61	3.096 (2)	117
N4—H4···N1ⁱ	0.86	2.55	3.339 (3)	153
C1—H1···O1ⁱⁱ	0.93	2.29	3.214 (3)	171
C13—H13···N1ⁱ	0.93	2.48	3.342 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁BrN₄OS
M_r	409.35
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.2061 (8), 9.521 (1), 14.2862 (16)
α, β, γ (°)	104.132 (1), 90.804 (1), 95.820 (1)
V (Å³)	944.84 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.30
Crystal size (mm)	0.25 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.597, 0.770
No. of measured, independent and observed [I > 2σ(I)] reflections	8793, 4076, 2644
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.092, 1.01
No. of reflections	4076
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.42

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···S1	0.86	2.61	3.096 (2)	116.7
N4—H4···N1ⁱ	0.86	2.55	3.339 (3)	153.1
C1—H1···O1ⁱⁱ	0.93	2.29	3.214 (3)	171.4
C13—H13···N1ⁱ	0.93	2.48	3.342 (3)	153.4

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

Acknowledgements

This work was supported by the Fund for Fostering Talents of Kunming University of Science and Technology (grant No. 14118149) and the Natural Science Foundation of Yunnan Province (grant No. 619120090059 to YPW) and the Western Light Talent Culture Project of the Chinese Academy of Sciences (grant No. W8090303 to YPH).

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Lin, R.-H., Connolly, P. J., Huang, S.-L., Wetter, S. K., Lu, Y.-H., Murray, W. V., Emanuel, S. L., Gruninger, R. H., Fuentes-Pesquera, A. R., Rugg, C. A., Middleton, S. A. & Jolliffe, L. K. (2005). J. Med. Chem. 48, 4208–4211. Web of Science CSD CrossRef PubMed CAS Google Scholar
Naito, Y., Akahoshi, F., Takeda, S., Okada, T., Kajii, M., Nishimura, H., Sugiura, M., Fukaya, C. & Kagitani, Y. (1996). J. Med. Chem. 39, 3019–3029. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sui, Z.-H., Guan, J.-H., Hlasta, D. J., Macielag, M. J., Foleno, B. D., Goldschmidt, R. M., Loeloff, M. J., Webb, G. C. & Barrett, J. F. (1998). Bioorg. Med. Chem. Lett. 8, 1929–1934. Web of Science CrossRef CAS PubMed Google Scholar
Tafi, A., Costi, R., Botta, M., Santo, R. D., Corelli, F., Massa, S., Ciacci, A., Manetti, F. & Artico, M. (2002). J. Med. Chem. 45, 2720–2732. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 68| Part 5| May 2012| Page o1495

doi:10.1107/S1600536812015991

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

N-(4-Bromo­phen­yl)-2-[(1-cyclo­hexyl­meth­yl-1H-1,2,4-triazol-3-yl)sulfanyl]­acetamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(4-Bromophenyl)-2-[(1-cyclohexylmethyl-1H-1,2,4-triazol-3-yl)sulfanyl]acetamide