Benzyl 3-[(E)-(furan-2-yl)methyl-idene]-2-methyldithio-carbazate.

In the title compound, C(14)H(14)N(2)OS(2), the furan ring exhibits rotational disorder over two orientations, with an occupancy ratio of 0.508 (7):0.492 (7). The furan and phenyl rings form dihedral angles of 8.2 (6) (major occupancy component), 14.8 (6) (minor occupancy component) and 73.65 (9)°, respectively, with the central residue (C(4)N(2)S(2)), indicating a twisted conformation for the mol-ecule. The methyl group and the thione S atom are syn and the conformation about the imine bond is E. In the crystal, C-H⋯π inter-actions involving the phenyl ring are observed.

Related literature

For background to the biological activity of S-containing ligands, see: Hazari et al. (2012 ▶). For related structures, see: Shan et al. (2008 ▶); Ganguly et al. (2011 ▶). For a similar compound with a thio­phene instead of a furan ring, see: Hazari et al. (2012 ▶).

Experimental

Crystal data

C14H14N2OS2

M = 290.39

Monoclinic,

a = 6.0415 (3) Å

b = 20.4840 (11) Å

c = 11.8959 (7) Å

β = 101.601 (5)°

V = 1442.09 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 298 K

0.5 × 0.5 × 0.3 mm

Data collection

Oxford Diffraction Gemini CCD S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.850, T max = 0.897

21725 measured reflections

3361 independent reflections

2393 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.090

S = 1.06

3361 reflections

219 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812035520/bh2449sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035520/bh2449Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035520/bh2449Isup3.cml

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

C14H14N2OS2	F(000) = 608
Mr = 290.39	Dx = 1.338 Mg m−3
Monoclinic, P21/n	Melting point: 432 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 6.0415 (3) Å	Cell parameters from 4212 reflections
b = 20.4840 (11) Å	θ = 4.0–28.9°
c = 11.8959 (7) Å	µ = 0.36 mm−1
β = 101.601 (5)°	T = 298 K
V = 1442.09 (14) Å3	Prism, green
Z = 4	0.5 × 0.5 × 0.3 mm

Oxford Diffraction Gemini CCD S Ultra diffractometer	3361 independent reflections
Graphite monochromator	2393 reflections with I > 2σ(I)
Detector resolution: 16.1158 pixels mm-1	Rint = 0.033
ω scans	θmax = 27.9°, θmin = 4.0°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −7→7
Tmin = 0.850, Tmax = 0.897	k = 0→26
21725 measured reflections	l = 0→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0275P)2 + 0.3918P] where P = (Fo2 + 2Fc2)/3
3361 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.16 e Å−3
12 restraints	Δρmin = −0.17 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.84126 (9)	0.20754 (3)	0.57831 (5)	0.06926 (18)
S2	0.99621 (8)	0.08488 (2)	0.71050 (4)	0.05239 (14)
N1	1.2300 (3)	0.19263 (7)	0.72613 (14)	0.0561 (4)
N2	1.3649 (2)	0.15222 (8)	0.80423 (13)	0.0554 (4)
C1	0.5997 (3)	−0.13887 (10)	0.66897 (17)	0.0637 (5)
H1A	0.5707	−0.1828	0.6791	0.076*
C2	0.7562 (4)	−0.12057 (10)	0.60675 (18)	0.0656 (5)
H2A	0.8344	−0.1522	0.5744	0.079*
C3	0.7987 (3)	−0.05537 (10)	0.59175 (17)	0.0605 (5)
H3A	0.9062	−0.0436	0.5494	0.073*
C4	0.6844 (3)	−0.00718 (9)	0.63849 (14)	0.0471 (4)
C5	0.5281 (3)	−0.02642 (10)	0.70175 (16)	0.0580 (5)
H5A	0.4504	0.005	0.735	0.07*
C6	0.4856 (3)	−0.09170 (11)	0.71639 (19)	0.0676 (6)
H6A	0.3786	−0.1039	0.7588	0.081*
C7	0.7263 (3)	0.06390 (9)	0.61993 (16)	0.0554 (5)
H7A	0.6067	0.0902	0.6403	0.066*
H7B	0.7302	0.0719	0.54	0.066*
C8	1.0304 (3)	0.16650 (9)	0.67204 (15)	0.0496 (4)
C9	1.3012 (4)	0.25833 (10)	0.7034 (2)	0.0813 (7)
H9A	1.1825	0.2797	0.6503	0.122*
H9B	1.4343	0.2561	0.671	0.122*
H9C	1.3339	0.2826	0.7738	0.122*
C10	1.5598 (3)	0.17332 (11)	0.85386 (18)	0.0663 (6)
H10A	1.6166	0.2134	0.8364	0.08*	0.508 (7)
H10B	1.5948	0.2156	0.8347	0.08*	0.492 (7)
O1	1.6236 (10)	0.0685 (3)	0.9740 (6)	0.0728 (16)	0.508 (7)
C11	1.691 (2)	0.1271 (8)	0.9441 (14)	0.055 (3)	0.508 (7)
C12	1.9117 (12)	0.1360 (5)	1.0053 (7)	0.081 (2)	0.508 (7)
H12A	2.0061	0.1716	1.003	0.097*	0.508 (7)
C13	1.960 (4)	0.0774 (10)	1.0732 (16)	0.083 (4)	0.508 (7)
H13A	2.095	0.0684	1.124	0.1*	0.508 (7)
C14	1.7950 (12)	0.0413 (4)	1.0535 (6)	0.088 (2)	0.508 (7)
H14A	1.7869	0.0008	1.0878	0.106*	0.508 (7)
O1'	1.9236 (7)	0.1675 (2)	0.9587 (4)	0.0668 (14)	0.492 (7)
C11'	1.720 (2)	0.1418 (9)	0.9281 (16)	0.054 (3)	0.492 (7)
C12'	1.6978 (18)	0.0874 (6)	0.9882 (9)	0.075 (2)	0.492 (7)
H12B	1.5713	0.0611	0.9855	0.09*	0.492 (7)
C13'	1.922 (5)	0.0804 (15)	1.058 (2)	0.112 (9)	0.492 (7)
H13B	1.969	0.0467	1.1097	0.134*	0.492 (7)
C14'	2.0407 (11)	0.1267 (4)	1.0379 (6)	0.078 (2)	0.492 (7)
H14B	2.1915	0.1324	1.073	0.093*	0.492 (7)

	U11	U22	U33	U12	U13	U23
S1	0.0677 (3)	0.0587 (3)	0.0773 (4)	0.0155 (2)	0.0048 (3)	0.0102 (3)
S2	0.0496 (3)	0.0497 (3)	0.0529 (3)	0.0008 (2)	−0.00161 (19)	0.0016 (2)
N1	0.0523 (9)	0.0497 (9)	0.0666 (10)	−0.0012 (7)	0.0124 (8)	−0.0024 (8)
N2	0.0479 (9)	0.0599 (9)	0.0573 (9)	0.0000 (7)	0.0082 (7)	−0.0103 (8)
C1	0.0673 (13)	0.0523 (12)	0.0684 (13)	−0.0010 (10)	0.0061 (10)	0.0024 (10)
C2	0.0726 (13)	0.0577 (12)	0.0690 (13)	0.0165 (10)	0.0201 (11)	−0.0040 (10)
C3	0.0589 (12)	0.0627 (13)	0.0638 (12)	0.0075 (9)	0.0218 (10)	0.0016 (10)
C4	0.0400 (9)	0.0520 (10)	0.0451 (9)	0.0031 (7)	−0.0014 (7)	−0.0034 (8)
C5	0.0487 (10)	0.0617 (12)	0.0637 (12)	0.0049 (9)	0.0116 (9)	−0.0107 (10)
C6	0.0597 (12)	0.0703 (14)	0.0767 (14)	−0.0065 (10)	0.0228 (11)	−0.0010 (11)
C7	0.0479 (10)	0.0534 (11)	0.0592 (11)	0.0034 (8)	−0.0027 (8)	0.0001 (9)
C8	0.0513 (10)	0.0489 (10)	0.0509 (10)	0.0061 (8)	0.0156 (8)	−0.0048 (8)
C9	0.0736 (15)	0.0534 (13)	0.120 (2)	−0.0069 (11)	0.0259 (14)	0.0048 (13)
C10	0.0540 (12)	0.0694 (13)	0.0745 (14)	−0.0052 (10)	0.0108 (10)	−0.0231 (11)
O1	0.064 (3)	0.081 (4)	0.066 (3)	0.006 (2)	−0.004 (2)	−0.003 (2)
C11	0.037 (3)	0.078 (10)	0.051 (6)	−0.010 (5)	0.008 (4)	−0.014 (4)
C12	0.053 (3)	0.100 (7)	0.083 (5)	−0.011 (4)	−0.002 (4)	−0.034 (4)
C13	0.070 (5)	0.102 (10)	0.068 (6)	0.018 (5)	−0.006 (4)	−0.022 (5)
C14	0.080 (5)	0.114 (6)	0.064 (3)	0.031 (4)	−0.003 (3)	−0.002 (4)
O1'	0.052 (2)	0.074 (3)	0.068 (3)	−0.0043 (19)	−0.0011 (17)	−0.0178 (19)
C11'	0.053 (5)	0.056 (5)	0.056 (5)	−0.015 (4)	0.019 (4)	−0.015 (3)
C12'	0.074 (6)	0.090 (7)	0.058 (4)	−0.007 (5)	0.007 (5)	−0.003 (4)
C13'	0.13 (2)	0.129 (14)	0.070 (7)	0.048 (13)	0.003 (9)	0.010 (9)
C14'	0.060 (3)	0.094 (5)	0.070 (4)	0.013 (3)	−0.007 (3)	−0.018 (3)

S1—C8	1.6562 (18)	C9—H9B	0.96
S2—C8	1.7566 (19)	C9—H9C	0.96
S2—C7	1.8161 (18)	C10—C11	1.529 (10)
N1—C8	1.357 (2)	C10—C11'	1.338 (11)
N1—N2	1.381 (2)	C10—H10A	0.93
N1—C9	1.455 (2)	C10—H10B	0.9299
N2—C10	1.281 (2)	O1—C11	1.338 (14)
C1—C2	1.365 (3)	O1—C14	1.373 (9)
C1—C6	1.372 (3)	C11—C12	1.396 (13)
C1—H1A	0.93	C12—C13	1.444 (18)
C2—C3	1.378 (3)	C12—H12A	0.93
C2—H2A	0.93	C13—C14	1.23 (3)
C3—C4	1.384 (2)	C13—H13A	0.93
C3—H3A	0.93	C14—H14A	0.93
C4—C5	1.378 (2)	O1'—C11'	1.320 (15)
C4—C7	1.502 (2)	O1'—C14'	1.349 (8)
C5—C6	1.379 (3)	C11'—C12'	1.347 (14)
C5—H5A	0.93	C12'—C13'	1.45 (2)
C6—H6A	0.93	C12'—H12B	0.93
C7—H7A	0.97	C13'—C14'	1.24 (3)
C7—H7B	0.97	C13'—H13B	0.93
C9—H9A	0.96	C14'—H14B	0.93
C8—S2—C7	102.08 (8)	H9A—C9—H9C	109.5
C8—N1—N2	115.50 (15)	H9B—C9—H9C	109.5
C8—N1—C9	123.00 (17)	N2—C10—C11'	128.2 (7)
N2—N1—C9	121.50 (16)	N2—C10—C11	114.4 (6)
C10—N2—N1	118.11 (17)	N2—C10—H10A	122.8
C2—C1—C6	119.30 (19)	C11'—C10—H10A	108.8
C2—C1—H1A	120.3	C11—C10—H10A	122.8
C6—C1—H1A	120.3	N2—C10—H10B	115.7
C1—C2—C3	120.25 (18)	C11'—C10—H10B	116.1
C1—C2—H2A	119.9	C11—C10—H10B	129.6
C3—C2—H2A	119.9	C11—O1—C14	108.6 (6)
C2—C3—C4	121.21 (18)	O1—C11—C12	106.8 (7)
C2—C3—H3A	119.4	O1—C11—C10	126.8 (9)
C4—C3—H3A	119.4	C12—C11—C10	126.3 (11)
C5—C4—C3	117.87 (18)	C11—C12—C13	104.3 (13)
C5—C4—C7	120.78 (17)	C11—C12—H12A	127.9
C3—C4—C7	121.35 (17)	C13—C12—H12A	127.9
C4—C5—C6	120.78 (18)	C14—C13—C12	109.3 (13)
C4—C5—H5A	119.6	C14—C13—H13A	125.4
C6—C5—H5A	119.6	C12—C13—H13A	125.4
C1—C6—C5	120.59 (19)	C13—C14—O1	111.0 (9)
C1—C6—H6A	119.7	C13—C14—H14A	124.5
C5—C6—H6A	119.7	O1—C14—H14A	124.5
C4—C7—S2	107.45 (12)	C11'—O1'—C14'	105.9 (6)
C4—C7—H7A	110.2	O1'—C11'—C10	120.0 (10)
S2—C7—H7A	110.2	O1'—C11'—C12'	111.8 (9)
C4—C7—H7B	110.2	C10—C11'—C12'	127.8 (13)
S2—C7—H7B	110.2	C11'—C12'—C13'	101.9 (15)
H7A—C7—H7B	108.5	C11'—C12'—H12B	129.1
N1—C8—S1	123.08 (14)	C13'—C12'—H12B	129.1
N1—C8—S2	113.05 (13)	C14'—C13'—C12'	108.9 (12)
S1—C8—S2	123.87 (11)	C14'—C13'—H13B	125.5
N1—C9—H9A	109.5	C12'—C13'—H13B	125.5
N1—C9—H9B	109.5	C13'—C14'—O1'	111.5 (9)
H9A—C9—H9B	109.5	C13'—C14'—H14B	124.3
N1—C9—H9C	109.5	O1'—C14'—H14B	124.3

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···Cgi	0.97	2.88	3.560 (2)	128
C13—H13A···Cgii	0.93	2.80	3.62 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

Table 1 ▶. Cg is the centroid of the phenyl ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯Cg i	0.97	2.88	3.560 (2)	128
C13—H13A⋯Cg ii	0.93	2.80	3.62 (2)	149

Symmetry codes: (i) ; (ii) .