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

The mol-ecule of the title Schiff base compound, C(7)H(8)N(2)OS(2), prepared by the reaction of methyl dithio-carbazate and furfural in an ethanol solution under reflux, adopts an E configuration; the dithio-carbazate and furan units are located on opposite sides of the C=N double bond. The planar dithio-carbazate group is twisted slightly with respect to the furan ring, making a dihedral angle of 5.2 (1)°. Adjacent mol-ecules are linked by N-H⋯S hydrogen bonding to form a supra-molecular dimer across an inversion center.

Related literature

For general background, see: Okabe et al. (1993 ▶); Shan et al. (2002 ▶, 2003 ▶). For a related structure, see: Chen et al. (2007 ▶). For the synthesis, see: Hu et al. (2001 ▶).

Experimental

Crystal data

C7H8N2OS2

M = 200.27

Triclinic,

a = 4.0866 (8) Å

b = 8.8698 (12) Å

c = 12.8453 (15) Å

α = 93.970 (14)°

β = 91.856 (12)°

γ = 98.293 (12)°

V = 459.21 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.53 mm−1

T = 294 (2) K

0.34 × 0.28 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.850, T max = 0.950 (expected range = 0.804–0.899)

4733 measured reflections

1608 independent reflections

1349 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.096

S = 1.09

1608 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.28 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/S1600536808012506/xu2417sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012506/xu2417Isup2.hkl

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

C7H8N2OS2	Z = 2
Mr = 200.27	F000 = 208
Triclinic, P1	Dx = 1.448 Mg m−3
Hall symbol: -P 1	Melting point = 414–416 K
a = 4.0866 (8) Å	Mo Kα radiation λ = 0.71073 Å
b = 8.8698 (12) Å	Cell parameters from 2276 reflections
c = 12.8453 (15) Å	θ = 2.0–25.0º
α = 93.970 (14)º	µ = 0.53 mm−1
β = 91.856 (12)º	T = 294 (2) K
γ = 98.293 (12)º	Prism, yellow
V = 459.21 (12) Å3	0.34 × 0.28 × 0.20 mm

Rigaku R-AXIS RAPID IP diffractometer	1608 independent reflections
Radiation source: fine-focus sealed tube	1349 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
Detector resolution: 10.0 pixels mm-1	θmax = 25.2º
T = 294(2) K	θmin = 1.6º
ω scans	h = −4→4
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	k = −10→10
Tmin = 0.850, Tmax = 0.950	l = −15→14
4733 measured reflections

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0598P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
1608 reflections	Δρmax = 0.19 e Å−3
110 parameters	Δρmin = −0.28 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	0.20815 (13)	0.27619 (5)	0.50863 (4)	0.0516 (2)
S2	0.38692 (13)	0.20142 (5)	0.28541 (4)	0.0506 (2)
N1	0.1859 (4)	0.45265 (16)	0.35473 (12)	0.0464 (4)
H1	0.1098	0.5149	0.3988	0.056*
N2	0.2353 (4)	0.49265 (16)	0.25394 (11)	0.0449 (4)
O1	0.3206 (4)	0.60245 (14)	0.05809 (10)	0.0553 (4)
C1	0.2537 (4)	0.3197 (2)	0.38518 (14)	0.0407 (4)
C2	0.4665 (5)	0.0393 (2)	0.35393 (17)	0.0557 (5)
H2A	0.6311	0.0720	0.4090	0.084*
H2B	0.5448	−0.0343	0.3062	0.084*
H2C	0.2659	−0.0063	0.3831	0.084*
C3	0.1483 (5)	0.6216 (2)	0.23454 (16)	0.0502 (5)
H3	0.0577	0.6772	0.2875	0.060*
C4	0.1847 (5)	0.6835 (2)	0.13501 (16)	0.0481 (5)
C5	0.1076 (7)	0.8131 (3)	0.09881 (19)	0.0685 (6)
H5	0.0139	0.8886	0.1360	0.082*
C6	0.1961 (6)	0.8126 (3)	−0.00661 (18)	0.0673 (6)
H6	0.1705	0.8873	−0.0523	0.081*
C7	0.3227 (6)	0.6849 (3)	−0.02770 (17)	0.0608 (6)
H7	0.4018	0.6557	−0.0920	0.073*

	U11	U22	U33	U12	U13	U23
S1	0.0714 (4)	0.0502 (3)	0.0359 (3)	0.0125 (2)	0.0107 (2)	0.0105 (2)
S2	0.0694 (4)	0.0482 (3)	0.0378 (3)	0.0171 (2)	0.0114 (2)	0.0072 (2)
N1	0.0681 (10)	0.0401 (8)	0.0326 (9)	0.0104 (7)	0.0108 (7)	0.0056 (7)
N2	0.0614 (10)	0.0393 (8)	0.0352 (9)	0.0078 (7)	0.0060 (7)	0.0077 (7)
O1	0.0837 (10)	0.0443 (7)	0.0418 (8)	0.0168 (7)	0.0145 (7)	0.0112 (6)
C1	0.0456 (10)	0.0405 (9)	0.0345 (10)	0.0013 (8)	0.0024 (8)	0.0026 (8)
C2	0.0701 (14)	0.0467 (11)	0.0534 (13)	0.0161 (9)	0.0056 (10)	0.0087 (9)
C3	0.0655 (13)	0.0478 (11)	0.0390 (11)	0.0114 (9)	0.0094 (9)	0.0051 (9)
C4	0.0631 (12)	0.0419 (10)	0.0419 (11)	0.0129 (9)	0.0072 (9)	0.0076 (8)
C5	0.0988 (17)	0.0596 (13)	0.0577 (14)	0.0391 (12)	0.0168 (12)	0.0165 (11)
C6	0.0947 (17)	0.0596 (13)	0.0544 (15)	0.0224 (12)	0.0054 (12)	0.0278 (11)
C7	0.0875 (16)	0.0583 (12)	0.0393 (12)	0.0115 (11)	0.0109 (10)	0.0173 (9)

S1—C1	1.6675 (18)	C2—H2B	0.9600
S2—C1	1.7500 (19)	C2—H2C	0.9600
S2—C2	1.800 (2)	C3—C4	1.430 (3)
N1—N2	1.379 (2)	C3—H3	0.9300
N1—C1	1.331 (2)	C4—C5	1.344 (3)
N1—H1	0.8600	C5—C6	1.413 (3)
N2—C3	1.284 (2)	C5—H5	0.9300
O1—C4	1.361 (2)	C6—C7	1.327 (4)
O1—C7	1.364 (2)	C6—H6	0.9300
C2—H2A	0.9600	C7—H7	0.9300
C1—S2—C2	101.98 (9)	N2—C3—C4	122.79 (19)
C1—N1—N2	121.34 (16)	N2—C3—H3	118.6
C1—N1—H1	119.3	C4—C3—H3	118.6
N2—N1—H1	119.3	C5—C4—O1	109.57 (17)
C3—N2—N1	114.59 (16)	C5—C4—C3	132.1 (2)
C4—O1—C7	106.45 (15)	O1—C4—C3	118.37 (16)
N1—C1—S1	120.76 (14)	C4—C5—C6	106.8 (2)
N1—C1—S2	114.05 (13)	C4—C5—H5	126.6
S1—C1—S2	125.19 (11)	C6—C5—H5	126.6
S2—C2—H2A	109.5	C7—C6—C5	106.67 (19)
S2—C2—H2B	109.5	C7—C6—H6	126.7
H2A—C2—H2B	109.5	C5—C6—H6	126.7
S2—C2—H2C	109.5	C6—C7—O1	110.5 (2)
H2A—C2—H2C	109.5	C6—C7—H7	124.8
H2B—C2—H2C	109.5	O1—C7—H7	124.8
C1—N1—N2—C3	177.62 (17)	N2—C3—C4—C5	179.2 (2)
N2—N1—C1—S1	177.32 (12)	N2—C3—C4—O1	−0.7 (3)
N2—N1—C1—S2	−3.0 (2)	O1—C4—C5—C6	0.7 (3)
C2—S2—C1—N1	178.23 (14)	C3—C4—C5—C6	−179.2 (2)
C2—S2—C1—S1	−2.13 (15)	C4—C5—C6—C7	−0.5 (3)
N1—N2—C3—C4	179.09 (17)	C5—C6—C7—O1	0.1 (3)
C7—O1—C4—C5	−0.6 (2)	C4—O1—C7—C6	0.3 (3)
C7—O1—C4—C3	179.25 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.86	2.65	3.4892 (17)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.86	2.65	3.4892 (17)	165

Symmetry code: (i) .