3-(4-Amino-3-methyl-5-sulfanyl-idene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-3-(2-fur-yl)-1-phenyl-propan-1-one.

In the title mol-ecule, C(16)H(16)N(4)O(2)S, the plane of the 1,2,4-triazole ring forms dihedral angles of 77.9 (2) and 30.0 (2)° with the planes of the furyl and phenyl rings, respectively. Weak inter-molecular N-H⋯S and C-H⋯O hydrogen bonds consolidate the crystal packing.

Related literature

For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivates, see: Al-Tamimi et al. (2010 ▶); Fun et al. (2009 ▶); Tan et al. (2010 ▶); Wang et al. (2011 ▶).

Experimental

Crystal data

C16H16N4O2S

M = 328.39

Monoclinic,

a = 7.3702 (8) Å

b = 24.131 (2) Å

c = 9.240 (1) Å

β = 106.745 (5)°

V = 1573.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.957, T max = 0.974

15993 measured reflections

3746 independent reflections

2835 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.119

S = 1.06

3746 reflections

217 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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) global, I. DOI: 10.1107/S1600536811020988/cv5087sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020988/cv5087Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020988/cv5087Isup3.cml

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

C16H16N4O2S	F(000) = 688
Mr = 328.39	Dx = 1.386 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4962 reflections
a = 7.3702 (8) Å	θ = 1.7–27.9°
b = 24.131 (2) Å	µ = 0.22 mm−1
c = 9.240 (1) Å	T = 113 K
β = 106.745 (5)°	Prism, colorless
V = 1573.7 (3) Å3	0.20 × 0.18 × 0.12 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	3746 independent reflections
Radiation source: rotating anode	2835 reflections with I > 2σ(I)
multilayer	Rint = 0.053
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.7°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −31→31
Tmin = 0.957, Tmax = 0.974	l = −12→10
15993 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0574P)2] where P = (Fo2 + 2Fc2)/3
3746 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.23 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
S1	0.32564 (7)	0.044074 (19)	0.12279 (6)	0.03395 (17)
O1	0.44017 (17)	0.24184 (5)	0.30582 (14)	0.0252 (3)
O2	0.76075 (17)	0.12393 (5)	0.14479 (15)	0.0302 (3)
N1	0.3805 (2)	0.13261 (6)	−0.04619 (17)	0.0216 (3)
N2	0.3656 (2)	0.14722 (6)	−0.19396 (18)	0.0266 (4)
N3	0.2807 (2)	0.06078 (6)	−0.17722 (18)	0.0298 (4)
N4	0.2143 (3)	0.00728 (7)	−0.2257 (2)	0.0447 (6)
H4A	0.312 (4)	−0.0188 (10)	−0.184 (3)	0.065 (8)*
H4B	0.120 (4)	0.0015 (10)	−0.184 (3)	0.054 (8)*
C1	0.3301 (2)	0.07965 (7)	−0.0317 (2)	0.0256 (4)
C2	0.3022 (3)	0.10221 (8)	−0.2710 (2)	0.0304 (5)
C3	0.4564 (2)	0.17151 (6)	0.0778 (2)	0.0196 (4)
H3	0.4213	0.1574	0.1679	0.023*
C4	0.3677 (2)	0.22862 (6)	0.0401 (2)	0.0219 (4)
H4C	0.4291	0.2481	−0.0277	0.026*
H4D	0.2315	0.2244	−0.0144	0.026*
C5	0.3886 (2)	0.26319 (7)	0.1805 (2)	0.0204 (4)
C6	0.3390 (2)	0.32323 (7)	0.1632 (2)	0.0199 (4)
C7	0.3636 (3)	0.35495 (7)	0.2932 (2)	0.0255 (4)
H7	0.4096	0.3380	0.3897	0.031*
C8	0.3215 (3)	0.41086 (7)	0.2828 (2)	0.0298 (5)
H8	0.3391	0.4324	0.3718	0.036*
C9	0.2533 (3)	0.43531 (7)	0.1412 (2)	0.0297 (5)
H9	0.2260	0.4738	0.1338	0.036*
C10	0.2250 (3)	0.40402 (7)	0.0111 (2)	0.0289 (4)
H10	0.1765	0.4209	−0.0852	0.035*
C11	0.2673 (3)	0.34799 (7)	0.0217 (2)	0.0251 (4)
H11	0.2475	0.3264	−0.0675	0.030*
C12	0.6687 (2)	0.17414 (7)	0.1194 (2)	0.0222 (4)
C13	0.7944 (3)	0.21587 (8)	0.1527 (2)	0.0310 (5)
H13	0.7673	0.2544	0.1447	0.037*
C14	0.9781 (3)	0.19038 (10)	0.2031 (2)	0.0388 (5)
H14	1.0966	0.2089	0.2356	0.047*
C15	0.9504 (3)	0.13569 (10)	0.1956 (2)	0.0384 (5)
H15	1.0483	0.1087	0.2219	0.046*
C16	0.2566 (3)	0.09657 (10)	−0.4376 (2)	0.0435 (6)
H16A	0.2883	0.1311	−0.4806	0.065*
H16B	0.1211	0.0889	−0.4801	0.065*
H16C	0.3303	0.0660	−0.4620	0.065*

	U11	U22	U33	U12	U13	U23
S1	0.0401 (3)	0.0202 (2)	0.0366 (3)	−0.00212 (19)	0.0030 (2)	0.0041 (2)
O1	0.0304 (7)	0.0238 (6)	0.0186 (7)	0.0022 (5)	0.0025 (5)	0.0014 (5)
O2	0.0255 (7)	0.0342 (7)	0.0290 (8)	0.0083 (5)	0.0051 (6)	0.0028 (6)
N1	0.0240 (8)	0.0204 (7)	0.0175 (9)	0.0025 (6)	0.0014 (6)	−0.0010 (6)
N2	0.0261 (8)	0.0324 (8)	0.0186 (9)	0.0048 (6)	0.0019 (7)	−0.0012 (7)
N3	0.0307 (9)	0.0222 (7)	0.0295 (10)	0.0064 (6)	−0.0028 (7)	−0.0095 (7)
N4	0.0461 (12)	0.0232 (8)	0.0509 (14)	0.0068 (8)	−0.0081 (11)	−0.0183 (9)
C1	0.0226 (9)	0.0205 (8)	0.0280 (11)	0.0051 (7)	−0.0017 (8)	−0.0039 (8)
C2	0.0243 (10)	0.0376 (10)	0.0247 (11)	0.0106 (8)	−0.0003 (8)	−0.0070 (9)
C3	0.0227 (9)	0.0179 (8)	0.0162 (10)	−0.0002 (7)	0.0027 (7)	−0.0023 (7)
C4	0.0260 (9)	0.0190 (8)	0.0180 (10)	0.0021 (7)	0.0021 (7)	0.0004 (7)
C5	0.0182 (8)	0.0217 (8)	0.0191 (10)	−0.0022 (7)	0.0015 (7)	−0.0008 (7)
C6	0.0184 (8)	0.0192 (8)	0.0212 (10)	−0.0006 (6)	0.0043 (7)	−0.0018 (7)
C7	0.0279 (10)	0.0268 (9)	0.0199 (10)	0.0026 (7)	0.0036 (8)	0.0013 (8)
C8	0.0361 (11)	0.0248 (9)	0.0272 (11)	0.0018 (8)	0.0070 (9)	−0.0055 (8)
C9	0.0374 (11)	0.0202 (9)	0.0320 (12)	0.0033 (8)	0.0106 (9)	−0.0013 (8)
C10	0.0366 (11)	0.0262 (9)	0.0238 (11)	0.0046 (8)	0.0087 (8)	0.0060 (8)
C11	0.0302 (10)	0.0235 (8)	0.0205 (11)	0.0014 (7)	0.0056 (8)	−0.0026 (7)
C12	0.0232 (9)	0.0259 (9)	0.0168 (10)	0.0034 (7)	0.0045 (7)	0.0011 (7)
C13	0.0342 (11)	0.0360 (10)	0.0243 (11)	−0.0091 (8)	0.0105 (9)	−0.0037 (8)
C14	0.0229 (10)	0.0715 (15)	0.0229 (11)	−0.0114 (10)	0.0079 (8)	−0.0037 (11)
C15	0.0207 (10)	0.0649 (15)	0.0277 (12)	0.0103 (10)	0.0038 (8)	0.0039 (11)
C16	0.0357 (12)	0.0648 (14)	0.0250 (13)	0.0099 (10)	0.0008 (9)	−0.0121 (11)

S1—C1	1.674 (2)	C6—C7	1.391 (2)
O1—C5	1.223 (2)	C6—C11	1.396 (2)
O2—C15	1.370 (2)	C7—C8	1.381 (2)
O2—C12	1.3755 (19)	C7—H7	0.9500
N1—C1	1.348 (2)	C8—C9	1.390 (3)
N1—N2	1.383 (2)	C8—H8	0.9500
N1—C3	1.462 (2)	C9—C10	1.383 (3)
N2—C2	1.309 (2)	C9—H9	0.9500
N3—C2	1.362 (3)	C10—C11	1.385 (2)
N3—C1	1.366 (2)	C10—H10	0.9500
N3—N4	1.407 (2)	C11—H11	0.9500
N4—H4A	0.95 (3)	C12—C13	1.343 (2)
N4—H4B	0.89 (2)	C13—C14	1.437 (3)
C2—C16	1.484 (3)	C13—H13	0.9500
C3—C12	1.501 (2)	C14—C15	1.334 (3)
C3—C4	1.522 (2)	C14—H14	0.9500
C3—H3	1.0000	C15—H15	0.9500
C4—C5	1.513 (2)	C16—H16A	0.9800
C4—H4C	0.9900	C16—H16B	0.9800
C4—H4D	0.9900	C16—H16C	0.9800
C5—C6	1.491 (2)
C15—O2—C12	106.30 (14)	C11—C6—C5	122.09 (16)
C1—N1—N2	113.18 (14)	C8—C7—C6	120.44 (17)
C1—N1—C3	125.81 (15)	C8—C7—H7	119.8
N2—N1—C3	120.89 (14)	C6—C7—H7	119.8
C2—N2—N1	103.86 (15)	C7—C8—C9	119.52 (18)
C2—N3—C1	109.54 (15)	C7—C8—H8	120.2
C2—N3—N4	124.36 (17)	C9—C8—H8	120.2
C1—N3—N4	126.09 (18)	C10—C9—C8	120.61 (16)
N3—N4—H4A	109.0 (14)	C10—C9—H9	119.7
N3—N4—H4B	104.4 (16)	C8—C9—H9	119.7
H4A—N4—H4B	108 (2)	C9—C10—C11	119.81 (17)
N1—C1—N3	102.79 (16)	C9—C10—H10	120.1
N1—C1—S1	130.11 (14)	C11—C10—H10	120.1
N3—C1—S1	127.09 (14)	C10—C11—C6	120.04 (17)
N2—C2—N3	110.62 (17)	C10—C11—H11	120.0
N2—C2—C16	125.36 (19)	C6—C11—H11	120.0
N3—C2—C16	124.02 (17)	C13—C12—O2	110.33 (16)
N1—C3—C12	111.29 (14)	C13—C12—C3	133.62 (16)
N1—C3—C4	111.10 (13)	O2—C12—C3	115.67 (14)
C12—C3—C4	111.56 (13)	C12—C13—C14	106.08 (18)
N1—C3—H3	107.6	C12—C13—H13	127.0
C12—C3—H3	107.6	C14—C13—H13	127.0
C4—C3—H3	107.6	C15—C14—C13	106.89 (18)
C5—C4—C3	111.85 (14)	C15—C14—H14	126.6
C5—C4—H4C	109.2	C13—C14—H14	126.6
C3—C4—H4C	109.2	C14—C15—O2	110.40 (17)
C5—C4—H4D	109.2	C14—C15—H15	124.8
C3—C4—H4D	109.2	O2—C15—H15	124.8
H4C—C4—H4D	107.9	C2—C16—H16A	109.5
O1—C5—C6	120.69 (16)	C2—C16—H16B	109.5
O1—C5—C4	120.43 (15)	H16A—C16—H16B	109.5
C6—C5—C4	118.85 (15)	C2—C16—H16C	109.5
C7—C6—C11	119.55 (15)	H16A—C16—H16C	109.5
C7—C6—C5	118.35 (16)	H16B—C16—H16C	109.5
C1—N1—N2—C2	0.83 (19)	O1—C5—C6—C7	3.7 (2)
C3—N1—N2—C2	177.05 (14)	C4—C5—C6—C7	−178.26 (15)
N2—N1—C1—N3	−0.38 (19)	O1—C5—C6—C11	−175.51 (16)
C3—N1—C1—N3	−176.37 (15)	C4—C5—C6—C11	2.5 (2)
N2—N1—C1—S1	179.91 (13)	C11—C6—C7—C8	−1.4 (3)
C3—N1—C1—S1	3.9 (3)	C5—C6—C7—C8	179.31 (16)
C2—N3—C1—N1	−0.21 (19)	C6—C7—C8—C9	0.3 (3)
N4—N3—C1—N1	−179.21 (17)	C7—C8—C9—C10	0.9 (3)
C2—N3—C1—S1	179.51 (14)	C8—C9—C10—C11	−0.9 (3)
N4—N3—C1—S1	0.5 (3)	C9—C10—C11—C6	−0.2 (3)
N1—N2—C2—N3	−0.94 (19)	C7—C6—C11—C10	1.4 (3)
N1—N2—C2—C16	178.24 (17)	C5—C6—C11—C10	−179.39 (16)
C1—N3—C2—N2	0.8 (2)	C15—O2—C12—C13	0.0 (2)
N4—N3—C2—N2	179.78 (17)	C15—O2—C12—C3	−173.96 (16)
C1—N3—C2—C16	−178.42 (17)	N1—C3—C12—C13	137.1 (2)
N4—N3—C2—C16	0.6 (3)	C4—C3—C12—C13	12.4 (3)
C1—N1—C3—C12	97.51 (19)	N1—C3—C12—O2	−50.8 (2)
N2—N1—C3—C12	−78.20 (18)	C4—C3—C12—O2	−175.52 (15)
C1—N1—C3—C4	−137.52 (17)	O2—C12—C13—C14	−0.2 (2)
N2—N1—C3—C4	46.8 (2)	C3—C12—C13—C14	172.20 (19)
N1—C3—C4—C5	159.98 (14)	C12—C13—C14—C15	0.4 (2)
C12—C3—C4—C5	−75.20 (19)	C13—C14—C15—O2	−0.4 (2)
C3—C4—C5—O1	−12.1 (2)	C12—O2—C15—C14	0.3 (2)
C3—C4—C5—C6	169.87 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···S1i	0.95 (3)	2.64 (3)	3.475 (2)	148 (2)
C4—H4D···O1ii	0.99	2.45	3.346 (2)	151
C14—H14···O1iii	0.95	2.55	3.490 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯S1i	0.95 (3)	2.64 (3)	3.475 (2)	148 (2)
C4—H4D⋯O1ii	0.99	2.45	3.346 (2)	151
C14—H14⋯O1iii	0.95	2.55	3.490 (2)	169

Symmetry codes: (i) ; (ii) ; (iii) .