2-[4-Benzyl-5-(2-fur-yl)-4H-1,2,4-triazol-3-ylsulfan-yl]acetamide.

In the title compound, C(15)H(14)N(4)O(2)S, the phenyl ring is inclined at 70.25 (6)° with respect to the approximately planar fur-yl-triazolsulfan-yl-acetamide unit. In the crystal structure, mol-ecules related by inversion centers form dimers via inter-molecular N-H⋯O hydrogen bonds between acetamide groups, resulting in eight-membered rings with an R(2) (2)(8) motif. In addition, the other H atom of the acetamide group is involved in an inter-molecular hydrogen bond with an N atom of the triazole ring, resulting in chains extended along the c axis. The overall effect is the formation of a hydrogen-bonded two-dimensional framework perpendicular to the a axis.

Related literature

For related literature, see: Ahmad et al. (2001 ▶); Altman & Solomost (1993 ▶); Bernstein et al. (1994 ▶); Chai et al. (2003 ▶); Dege et al. (2004 ▶); Hashimoto et al. (1990 ▶); Kanazawa et al. (1988 ▶); Yildirim et al. (2004 ▶); Zareef, Iqbal & Parvez (2008 ▶); Zareef, Iqbal, Mirza et al. (2008 ▶); Öztürk et al. (2004 ▶).

Experimental

Crystal data

C15H14N4O2S

M = 314.36

Monoclinic,

a = 15.995 (9) Å

b = 7.261 (3) Å

c = 13.598 (8) Å

β = 105.46 (2)°

V = 1522.1 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 (2) K

0.24 × 0.08 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.948, T max = 0.995

5255 measured reflections

3435 independent reflections

2449 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.105

S = 1.04

3435 reflections

206 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.26 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SAPI91 (Fan, 1991 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017170/lh2638sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017170/lh2638Isup2.hkl

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

C15H14N4O2S	F000 = 656
Mr = 314.36	Dx = 1.372 Mg m−3
Monoclinic, P21/c	Melting point = 417–419 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 15.995 (9) Å	Cell parameters from 5255 reflections
b = 7.261 (3) Å	θ = 3.2–27.5º
c = 13.598 (8) Å	µ = 0.23 mm−1
β = 105.46 (2)º	T = 173 (2) K
V = 1522.1 (14) Å3	Plate, colorless
Z = 4	0.24 × 0.08 × 0.02 mm

Nonius KappaCCD diffractometer	3435 independent reflections
Radiation source: fine-focus sealed tube	2449 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 173(2) K	θmax = 27.5º
ω and φ scans	θmin = 3.2º
Absorption correction: Multi-scan(SORTAV; Blessing, 1997)	h = −20→20
Tmin = 0.948, Tmax = 0.995	k = −9→7
5255 measured reflections	l = −17→17

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.045	w = 1/[σ2(Fo2) + (0.034P)2 + 0.75P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.105	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.28 e Å−3
3435 reflections	Δρmin = −0.26 e Å−3
206 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0052 (16)
Secondary atom site location: difference Fourier map

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
S1	0.12862 (3)	0.04606 (6)	0.49096 (4)	0.02689 (16)
O1	0.29228 (9)	0.72417 (18)	0.45345 (11)	0.0318 (4)
O2	0.07346 (10)	−0.29345 (18)	0.53495 (11)	0.0330 (4)
N1	0.14752 (11)	0.4036 (2)	0.28542 (12)	0.0290 (4)
N2	0.11490 (11)	0.2402 (2)	0.31391 (12)	0.0287 (4)
N3	0.19418 (10)	0.3766 (2)	0.45331 (11)	0.0219 (4)
N4	−0.01125 (12)	−0.3863 (2)	0.38142 (14)	0.0280 (4)
H4A	−0.0253 (14)	−0.489 (3)	0.4074 (17)	0.034*
H4B	−0.0375 (14)	−0.358 (3)	0.3169 (18)	0.034*
C1	0.23596 (13)	0.6584 (3)	0.36615 (16)	0.0279 (5)
C2	0.22942 (15)	0.7781 (3)	0.28834 (17)	0.0335 (5)
H2	0.1947	0.7646	0.2202	0.040*
C3	0.28508 (15)	0.9285 (3)	0.32900 (18)	0.0367 (5)
H3	0.2950	1.0347	0.2929	0.044*
C4	0.32076 (15)	0.8915 (3)	0.42773 (18)	0.0355 (5)
H4	0.3602	0.9699	0.4736	0.043*
C5	0.19400 (13)	0.4820 (3)	0.36896 (15)	0.0239 (4)
C6	0.14400 (13)	0.2270 (2)	0.41377 (15)	0.0236 (4)
C7	0.05176 (13)	−0.0836 (2)	0.39448 (15)	0.0243 (4)
H7A	−0.0038	−0.0160	0.3718	0.029*
H7B	0.0747	−0.1049	0.3346	0.029*
C8	0.03843 (13)	−0.2653 (3)	0.44313 (15)	0.0246 (4)
C9	0.23541 (13)	0.4072 (3)	0.56249 (14)	0.0250 (4)
H9A	0.1943	0.3721	0.6023	0.030*
H9B	0.2486	0.5399	0.5742	0.030*
C10	0.31828 (13)	0.2975 (3)	0.60034 (14)	0.0250 (4)
C11	0.32270 (15)	0.1562 (3)	0.66992 (16)	0.0355 (5)
H11	0.2734	0.1278	0.6934	0.043*
C12	0.39864 (17)	0.0557 (3)	0.70563 (19)	0.0484 (6)
H12	0.4012	−0.0407	0.7536	0.058*
C13	0.47022 (17)	0.0959 (4)	0.6714 (2)	0.0501 (7)
H13	0.5222	0.0273	0.6959	0.060*
C14	0.46651 (15)	0.2352 (3)	0.6017 (2)	0.0437 (6)
H14	0.5159	0.2621	0.5779	0.052*
C15	0.39075 (14)	0.3365 (3)	0.56616 (17)	0.0344 (5)
H15	0.3885	0.4329	0.5183	0.041*

	U11	U22	U33	U12	U13	U23
S1	0.0291 (3)	0.0266 (3)	0.0229 (3)	−0.0040 (2)	0.0033 (2)	0.0036 (2)
O1	0.0348 (8)	0.0264 (7)	0.0321 (8)	−0.0040 (6)	0.0055 (7)	0.0003 (6)
O2	0.0390 (9)	0.0298 (7)	0.0253 (8)	−0.0067 (7)	0.0000 (7)	0.0067 (6)
N1	0.0328 (10)	0.0305 (8)	0.0239 (9)	−0.0027 (8)	0.0080 (8)	0.0029 (7)
N2	0.0326 (10)	0.0296 (8)	0.0227 (9)	−0.0040 (8)	0.0051 (8)	0.0024 (7)
N3	0.0218 (9)	0.0233 (8)	0.0198 (8)	0.0000 (7)	0.0041 (7)	0.0006 (6)
N4	0.0366 (11)	0.0223 (8)	0.0234 (9)	−0.0018 (8)	0.0050 (8)	0.0033 (7)
C1	0.0263 (11)	0.0291 (10)	0.0292 (11)	0.0009 (9)	0.0093 (9)	−0.0014 (8)
C2	0.0378 (13)	0.0334 (11)	0.0302 (12)	−0.0015 (10)	0.0106 (10)	0.0049 (9)
C3	0.0428 (14)	0.0289 (11)	0.0433 (14)	−0.0009 (10)	0.0203 (11)	0.0070 (10)
C4	0.0368 (13)	0.0225 (10)	0.0505 (15)	−0.0056 (9)	0.0176 (12)	−0.0035 (9)
C5	0.0244 (10)	0.0256 (9)	0.0225 (10)	0.0027 (8)	0.0077 (9)	0.0012 (8)
C6	0.0224 (10)	0.0257 (9)	0.0224 (11)	0.0002 (8)	0.0053 (9)	−0.0011 (8)
C7	0.0263 (11)	0.0229 (9)	0.0230 (10)	−0.0020 (8)	0.0053 (9)	0.0013 (8)
C8	0.0253 (11)	0.0241 (9)	0.0241 (11)	0.0041 (8)	0.0060 (9)	0.0028 (8)
C9	0.0256 (11)	0.0289 (10)	0.0205 (10)	−0.0023 (9)	0.0060 (9)	−0.0022 (8)
C10	0.0251 (11)	0.0272 (10)	0.0200 (10)	−0.0004 (8)	0.0012 (9)	−0.0052 (8)
C11	0.0348 (13)	0.0403 (12)	0.0285 (12)	0.0038 (11)	0.0036 (10)	0.0031 (10)
C12	0.0476 (16)	0.0499 (14)	0.0406 (15)	0.0118 (13)	−0.0004 (12)	0.0127 (11)
C13	0.0333 (14)	0.0514 (14)	0.0559 (17)	0.0104 (12)	−0.0050 (13)	−0.0021 (13)
C14	0.0252 (12)	0.0450 (13)	0.0591 (17)	−0.0014 (11)	0.0081 (12)	−0.0083 (12)
C15	0.0284 (12)	0.0326 (11)	0.0412 (14)	−0.0018 (10)	0.0076 (10)	0.0009 (9)

S1—C6	1.740 (2)	C3—H3	0.9500
S1—C7	1.805 (2)	C4—H4	0.9500
O1—C1	1.371 (2)	C7—C8	1.516 (3)
O1—C4	1.375 (2)	C7—H7A	0.9900
O2—C8	1.242 (2)	C7—H7B	0.9900
N1—C5	1.310 (3)	C9—C10	1.514 (3)
N1—N2	1.392 (2)	C9—H9A	0.9900
N2—C6	1.316 (3)	C9—H9B	0.9900
N3—C6	1.372 (2)	C10—C11	1.385 (3)
N3—C5	1.378 (2)	C10—C15	1.388 (3)
N3—C9	1.472 (2)	C11—C12	1.389 (3)
N4—C8	1.324 (3)	C11—H11	0.9500
N4—H4A	0.88 (2)	C12—C13	1.377 (4)
N4—H4B	0.89 (2)	C12—H12	0.9500
C1—C2	1.351 (3)	C13—C14	1.376 (4)
C1—C5	1.452 (3)	C13—H13	0.9500
C2—C3	1.424 (3)	C14—C15	1.390 (3)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.339 (3)	C15—H15	0.9500
C6—S1—C7	97.69 (9)	C8—C7—H7B	110.4
C1—O1—C4	105.85 (16)	S1—C7—H7B	110.4
C5—N1—N2	107.29 (16)	H7A—C7—H7B	108.6
C6—N2—N1	107.04 (15)	O2—C8—N4	124.19 (18)
C6—N3—C5	104.00 (16)	O2—C8—C7	120.25 (17)
C6—N3—C9	124.93 (15)	N4—C8—C7	115.56 (17)
C5—N3—C9	131.06 (16)	N3—C9—C10	112.32 (15)
C8—N4—H4A	118.8 (14)	N3—C9—H9A	109.1
C8—N4—H4B	121.1 (14)	C10—C9—H9A	109.1
H4A—N4—H4B	119 (2)	N3—C9—H9B	109.1
C2—C1—O1	110.49 (18)	C10—C9—H9B	109.1
C2—C1—C5	130.4 (2)	H9A—C9—H9B	107.9
O1—C1—C5	119.10 (17)	C11—C10—C15	119.0 (2)
C1—C2—C3	106.2 (2)	C11—C10—C9	120.18 (19)
C1—C2—H2	126.9	C15—C10—C9	120.82 (18)
C3—C2—H2	126.9	C10—C11—C12	120.6 (2)
C4—C3—C2	106.91 (19)	C10—C11—H11	119.7
C4—C3—H3	126.5	C12—C11—H11	119.7
C2—C3—H3	126.5	C13—C12—C11	119.9 (2)
C3—C4—O1	110.53 (19)	C13—C12—H12	120.0
C3—C4—H4	124.7	C11—C12—H12	120.0
O1—C4—H4	124.7	C14—C13—C12	120.1 (2)
N1—C5—N3	110.81 (17)	C14—C13—H13	120.0
N1—C5—C1	121.34 (18)	C12—C13—H13	120.0
N3—C5—C1	127.84 (18)	C13—C14—C15	120.1 (2)
N2—C6—N3	110.85 (16)	C13—C14—H14	119.9
N2—C6—S1	127.53 (15)	C15—C14—H14	119.9
N3—C6—S1	121.56 (14)	C10—C15—C14	120.3 (2)
C8—C7—S1	106.52 (13)	C10—C15—H15	119.9
C8—C7—H7A	110.4	C14—C15—H15	119.9
S1—C7—H7A	110.4
C5—N1—N2—C6	−0.5 (2)	C9—N3—C6—N2	178.80 (17)
C4—O1—C1—C2	0.4 (2)	C5—N3—C6—S1	176.91 (14)
C4—O1—C1—C5	−179.59 (18)	C9—N3—C6—S1	−3.8 (3)
O1—C1—C2—C3	0.1 (2)	C7—S1—C6—N2	−7.9 (2)
C5—C1—C2—C3	−180.0 (2)	C7—S1—C6—N3	175.14 (16)
C1—C2—C3—C4	−0.5 (3)	C6—S1—C7—C8	172.23 (13)
C2—C3—C4—O1	0.7 (3)	S1—C7—C8—O2	4.6 (2)
C1—O1—C4—C3	−0.7 (2)	S1—C7—C8—N4	−175.01 (15)
N2—N1—C5—N3	0.2 (2)	C6—N3—C9—C10	79.9 (2)
N2—N1—C5—C1	−178.64 (17)	C5—N3—C9—C10	−101.0 (2)
C6—N3—C5—N1	0.2 (2)	N3—C9—C10—C11	−113.1 (2)
C9—N3—C5—N1	−179.06 (18)	N3—C9—C10—C15	66.9 (2)
C6—N3—C5—C1	178.91 (19)	C15—C10—C11—C12	0.4 (3)
C9—N3—C5—C1	−0.3 (3)	C9—C10—C11—C12	−179.5 (2)
C2—C1—C5—N1	7.9 (3)	C10—C11—C12—C13	−0.3 (4)
O1—C1—C5—N1	−172.15 (18)	C11—C12—C13—C14	−0.1 (4)
C2—C1—C5—N3	−170.7 (2)	C12—C13—C14—C15	0.4 (4)
O1—C1—C5—N3	9.3 (3)	C11—C10—C15—C14	−0.2 (3)
N1—N2—C6—N3	0.6 (2)	C9—C10—C15—C14	179.81 (19)
N1—N2—C6—S1	−176.61 (15)	C13—C14—C15—C10	−0.2 (3)
C5—N3—C6—N2	−0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2i	0.88 (2)	2.01 (2)	2.880 (2)	172 (2)
N4—H4B···N2ii	0.89 (2)	2.01 (2)	2.881 (3)	167 (2)
C9—H9B···O1	0.99	2.36	3.007 (3)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O2i	0.88 (2)	2.01 (2)	2.880 (2)	172 (2)
N4—H4B⋯N2ii	0.89 (2)	2.01 (2)	2.881 (3)	167 (2)
C9—H9B⋯O1	0.99	2.36	3.007 (3)	122

Symmetry codes: (i) ; (ii) .