Benzyl 3-[(E)-furfuryl-idene]dithio-carbazate.

In the title compound, C(13)H(12)N(2)OS(2), the mol-ecule assumes an E configuration, with the furan ring and dithio-carbazate units located on opposite sides of the N=C double bond. In the crystal structure, mol-ecules are linked via two inter-molecular N-H⋯S hydrogen bonds to form centrosymmetric dimers.

Related literature

For general background, see: Okabe et al. (1993 ▶). For related structures, see: Shan et al. (2006 ▶, 2008 ▶). For the synthesis and background, see: Hu et al. (2001 ▶).

Experimental

Crystal data

C13H12N2OS2

M = 276.37

Triclinic,

a = 4.8331 (11) Å

b = 12.040 (3) Å

c = 12.549 (3) Å

α = 108.203 (7)°

β = 99.704 (9)°

γ = 97.910 (8)°

V = 669.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.39 mm−1

T = 295 (2) K

0.42 × 0.36 × 0.32 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: none

7084 measured reflections

2324 independent reflections

1799 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.07

2324 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801307X/hb2727sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801307X/hb2727Isup2.hkl

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

C13H12N2OS2	Z = 2
Mr = 276.37	F000 = 288
Triclinic, P1	Dx = 1.371 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 4.8331 (11) Å	Cell parameters from 3836 reflections
b = 12.040 (3) Å	θ = 1.8–25.0º
c = 12.549 (3) Å	µ = 0.39 mm−1
α = 108.203 (7)º	T = 295 (2) K
β = 99.704 (9)º	Prism, yellow
γ = 97.910 (8)º	0.42 × 0.36 × 0.32 mm
V = 669.5 (3) Å3

Rigaku R-AXIS RAPID IP diffractometer	2324 independent reflections
Radiation source: fine-focus sealed tube	1799 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
Detector resolution: 10.00 pixels mm-1	θmax = 25.0º
T = 295(2) K	θmin = 1.8º
ω scans	h = −5→5
Absorption correction: none	k = −14→13
7084 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0446P)2 + 0.0525P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2324 reflections	Δρmax = 0.14 e Å−3
163 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	1.03544 (13)	−0.02756 (5)	0.32307 (4)	0.0669 (2)
S2	0.84716 (12)	0.18647 (4)	0.27822 (4)	0.06143 (19)
O1	0.4143 (3)	0.41877 (12)	0.56065 (11)	0.0662 (4)
N1	0.6602 (3)	0.22213 (13)	0.48240 (13)	0.0533 (4)
N2	0.7837 (3)	0.12309 (13)	0.45371 (13)	0.0569 (4)
H2N	0.7943	0.0807	0.4976	0.068*
C1	0.4147 (4)	0.33502 (16)	0.61307 (15)	0.0527 (5)
C2	0.2854 (5)	0.36601 (19)	0.70185 (17)	0.0640 (5)
H2	0.2592	0.3242	0.7516	0.077*
C3	0.1967 (5)	0.47383 (19)	0.70534 (19)	0.0711 (6)
H3	0.1011	0.5168	0.7574	0.085*
C4	0.2776 (5)	0.50159 (19)	0.61914 (19)	0.0720 (6)
H4	0.2452	0.5687	0.6011	0.086*
C5	0.5457 (4)	0.23599 (17)	0.56929 (16)	0.0548 (5)
H5	0.5479	0.1793	0.6054	0.066*
C6	0.8870 (4)	0.09223 (16)	0.35868 (15)	0.0510 (5)
C7	1.0091 (5)	0.11971 (19)	0.15901 (17)	0.0647 (5)
H7A	1.2107	0.1229	0.1872	0.078*
H7B	0.9145	0.0368	0.1189	0.078*
C8	0.9740 (4)	0.19026 (17)	0.07913 (16)	0.0560 (5)
C9	0.7422 (5)	0.1560 (2)	−0.01297 (19)	0.0764 (6)
H9	0.6064	0.0877	−0.0258	0.092*
C10	0.7056 (7)	0.2192 (3)	−0.0861 (2)	0.0916 (8)
H10	0.5469	0.1939	−0.1476	0.110*
C11	0.9002 (8)	0.3183 (3)	−0.0689 (3)	0.0931 (9)
H11	0.8750	0.3616	−0.1182	0.112*
C12	1.1348 (7)	0.3554 (2)	0.0210 (3)	0.0979 (9)
H12	1.2695	0.4235	0.0325	0.117*
C13	1.1712 (5)	0.2906 (2)	0.0954 (2)	0.0795 (6)
H13	1.3306	0.3159	0.1565	0.095*

	U11	U22	U33	U12	U13	U23
S1	0.0906 (4)	0.0557 (3)	0.0675 (3)	0.0399 (3)	0.0222 (3)	0.0265 (2)
S2	0.0790 (4)	0.0596 (3)	0.0632 (3)	0.0369 (3)	0.0240 (3)	0.0313 (2)
O1	0.0945 (11)	0.0586 (8)	0.0640 (8)	0.0373 (7)	0.0296 (7)	0.0313 (7)
N1	0.0610 (10)	0.0490 (9)	0.0560 (9)	0.0254 (8)	0.0127 (8)	0.0206 (7)
N2	0.0722 (11)	0.0519 (9)	0.0595 (9)	0.0302 (8)	0.0188 (8)	0.0275 (7)
C1	0.0573 (12)	0.0517 (11)	0.0549 (10)	0.0174 (9)	0.0118 (9)	0.0244 (9)
C2	0.0741 (14)	0.0667 (13)	0.0656 (12)	0.0244 (11)	0.0285 (11)	0.0316 (10)
C3	0.0787 (15)	0.0672 (14)	0.0736 (14)	0.0314 (12)	0.0303 (12)	0.0187 (11)
C4	0.0920 (17)	0.0575 (13)	0.0773 (14)	0.0389 (12)	0.0243 (12)	0.0253 (11)
C5	0.0623 (12)	0.0526 (11)	0.0585 (11)	0.0213 (9)	0.0138 (9)	0.0275 (9)
C6	0.0525 (11)	0.0483 (11)	0.0547 (10)	0.0173 (9)	0.0079 (8)	0.0201 (8)
C7	0.0737 (14)	0.0654 (13)	0.0702 (12)	0.0341 (11)	0.0265 (11)	0.0303 (10)
C8	0.0629 (13)	0.0559 (12)	0.0600 (11)	0.0263 (10)	0.0251 (10)	0.0229 (9)
C9	0.0843 (17)	0.0717 (15)	0.0764 (14)	0.0172 (12)	0.0151 (13)	0.0309 (12)
C10	0.117 (2)	0.100 (2)	0.0697 (15)	0.0416 (18)	0.0182 (14)	0.0385 (15)
C11	0.132 (3)	0.103 (2)	0.0922 (19)	0.065 (2)	0.0647 (19)	0.0602 (17)
C12	0.103 (2)	0.0752 (17)	0.142 (3)	0.0230 (16)	0.062 (2)	0.0551 (18)
C13	0.0761 (16)	0.0753 (16)	0.0940 (16)	0.0195 (13)	0.0238 (13)	0.0346 (13)

S1—C6	1.6686 (18)	C5—H5	0.9300
S2—C6	1.7477 (19)	C7—C8	1.507 (3)
S2—C7	1.820 (2)	C7—H7A	0.9700
O1—C4	1.363 (2)	C7—H7B	0.9700
O1—C1	1.365 (2)	C8—C13	1.369 (3)
N1—C5	1.280 (2)	C8—C9	1.378 (3)
N1—N2	1.381 (2)	C9—C10	1.369 (3)
N2—C6	1.336 (2)	C9—H9	0.9300
N2—H2N	0.8600	C10—C11	1.348 (4)
C1—C2	1.345 (3)	C10—H10	0.9300
C1—C5	1.428 (3)	C11—C12	1.368 (4)
C2—C3	1.412 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.395 (4)
C3—C4	1.329 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—H4	0.9300
C6—S2—C7	102.07 (9)	C8—C7—S2	107.15 (13)
C4—O1—C1	106.12 (15)	C8—C7—H7A	110.3
C5—N1—N2	114.92 (16)	S2—C7—H7A	110.3
C6—N2—N1	120.90 (15)	C8—C7—H7B	110.3
C6—N2—H2N	119.6	S2—C7—H7B	110.3
N1—N2—H2N	119.6	H7A—C7—H7B	108.5
C2—C1—O1	109.46 (17)	C13—C8—C9	117.6 (2)
C2—C1—C5	131.99 (18)	C13—C8—C7	121.2 (2)
O1—C1—C5	118.55 (16)	C9—C8—C7	121.1 (2)
C1—C2—C3	107.23 (19)	C10—C9—C8	122.0 (2)
C1—C2—H2	126.4	C10—C9—H9	119.0
C3—C2—H2	126.4	C8—C9—H9	119.0
C4—C3—C2	106.14 (18)	C11—C10—C9	119.8 (3)
C4—C3—H3	126.9	C11—C10—H10	120.1
C2—C3—H3	126.9	C9—C10—H10	120.1
C3—C4—O1	111.05 (19)	C10—C11—C12	120.3 (3)
C3—C4—H4	124.5	C10—C11—H11	119.9
O1—C4—H4	124.5	C12—C11—H11	119.9
N1—C5—C1	122.66 (18)	C11—C12—C13	119.7 (3)
N1—C5—H5	118.7	C11—C12—H12	120.1
C1—C5—H5	118.7	C13—C12—H12	120.1
N2—C6—S1	121.22 (14)	C8—C13—C12	120.5 (2)
N2—C6—S2	114.01 (13)	C8—C13—H13	119.7
S1—C6—S2	124.76 (11)	C12—C13—H13	119.7

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···S1i	0.86	2.56	3.3761 (19)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯S1i	0.86	2.56	3.3761 (19)	158

Symmetry code: (i) .