N-(4-Bromo-phen-yl)-2-[(1-cyclo-hexyl-meth-yl-1H-1,2,4-triazol-3-yl)sulfanyl]-acetamide.

The title compound, C(17)H(21)BrN(4)OS, 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, mol-ecules 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 inter-actions.

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 = 409.35

Triclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.092

S = 1.01

4076 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.42 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015991/bq2348sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H21BrN4OS	Z = 2
Mr = 409.35	F(000) = 420
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0382P)2 + 0.1448P] where P = (Fo2 + 2Fc2)/3
4076 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .