3-(4-Amino-3-methyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-3-(2-fur­yl)-1-phenyl­propan-1-one

Gao, Y.; Wang, L.; Wang, H.

doi:10.1107/S1600536811020988

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1609

doi:10.1107/S1600536811020988

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3-(4-Amino-3-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-3-(2-furyl)-1-phenylpropan-1-one

Yan Gao,^a Lu Wang ^b and He-wen Wang ^c ^*

^aSchool of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, People's Republic of China, ^bCollege of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, People's Republic of China, and ^cCollege of Chemistry and Applied Chemistry, Huanggang Normal University, Huanggang 438000, People's Republic of China
^*Correspondence e-mail: zhao_submit@yahoo.com.cn

(Received 30 April 2011; accepted 31 May 2011; online 11 June 2011)

In the title molecule, C₁₆H₁₆N₄O₂S, 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 intermolecular 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_r = 328.39
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.119
S = 1.06
3746 reflections
217 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) -x+1, -y, -z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x+1, y, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020988/cv5087sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811020988/cv5087Isup3.cml

checkCIF report

Comment top

In continuation of structural study of 1,2,4-triazole-5(4H)-thione derivatives in our group (Wang et al., 2011), we present here the crystal structure of the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles are normal and comparable with those reported for the related 1,2,4-triazole-5(4H)- thione derivatives (Al-Tamimi et al., 2010; Fun et al., 2009; Tan et al., 2010; Wang et al., 2011). The 1,2,4-triazole ring makes the dihedral angles of 30.2 (2) and 77.9 (2)° with the phenyl ring and the furanyl ring, respectively. The phenyl and furanyl rings form a dihedral angle of 71.1 (2) °.

Intermolecular N—H···S hydrogen bond (Table 1) links the adjacent molecule into centrosymmetric dimers, which are further linked by the weak C—H···O interactions (Table 1) into three-dimensional structure.

Related literature top

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 top

The title compound was synthesized by the reaction of the 3-(furan-2-yl)-1- phenyl-2-propen-1-one (2.0 mmol) with 4-amino-3-methyl-4H-1,2,4-triazole-5- thiol (2.0 mmol) in ethanol. The reaction progress was monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as colorless solid in 84% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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. View of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 55% probability level.

3-(4-Amino-3-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl)- 3-(2-furyl)-1-phenylpropan-1-one top

Crystal data top

C₁₆H₁₆N₄O₂S	F(000) = 688
M_r = 328.39	D_x = 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

Data collection top

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

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)] = 0.049	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(F_o²) + (0.0574P)²] where P = (F_o² + 2F_c²)/3
3746 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₆H₁₆N₄O₂S	V = 1573.7 (3) Å³
M_r = 328.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.3702 (8) Å	µ = 0.22 mm⁻¹
b = 24.131 (2) Å	T = 113 K
c = 9.240 (1) Å	0.20 × 0.18 × 0.12 mm
β = 106.745 (5)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3746 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2835 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.974	R_int = 0.053
15993 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.37 e Å⁻³
3746 reflections	Δρ_min = −0.23 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₄O₂S
M_r	328.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	7.3702 (8), 24.131 (2), 9.240 (1)
β (°)	106.745 (5)
V (Å³)	1573.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.957, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	15993, 3746, 2835
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.119, 1.06
No. of reflections	3746
No. of parameters	217
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.23

Computer programs: CrystalClear (Rigaku/MSC, 2005), 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—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) −x+1, −y, −z; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1, y, z.

References

Al-Tamimi, A.-M. S., Bari, A., Al-Omar, M. A., Alrashood, K. A. & El-Emam, A. A. (2010). Acta Cryst. E66, o1756. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Chantrapromma, S., Sujith, K. V. & Kalluraya, B. (2009). Acta Cryst. E65, o495–o496. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tan, K. W., Maah, M. J. & Ng, S. W. (2010). Acta Cryst. E66, o2224. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, W., Gao, Y., Xiao, Z., Yao, H. & Zhang, J. (2011). Acta Cryst. E67, o269. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page o1609

doi:10.1107/S1600536811020988

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

3-(4-Amino-3-methyl-5-sulfanyl­­idene-4,5-di­hydro-1H-1,2,4-triazol-1-yl)-3-(2-fur­yl)-1-phenyl­propan-1-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

3-(4-Amino-3-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-3-(2-furyl)-1-phenylpropan-1-one