organic compounds
Benzyl 3-[(E)-(furan-2-yl)methylidene]-2-methyldithiocarbazate
aUniversity of Chittagong, Chittagong 4331, Bangladesh, and bDepartamento de Química Inorgánica Analítica y Química Física, INQUIMAE-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina
*Correspondence e-mail: tapashir57@gmail.com
In the title compound, C14H14N2OS2, 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 (C4N2S2), indicating a twisted conformation for the molecule. 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 interactions 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
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell 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).
Supporting information
10.1107/S1600536812035520/bh2449sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812035520/bh2449Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812035520/bh2449Isup3.cml
Single crystals of the title compound were prepared by following three steps.
Step 1 (Hazari et al., 2012). Synthesis of N-methyl-S-benzyldithiocarbazate. Potassium hydroxide (11.5 g) was dissolved in 60 ml of 90% ethanol and the mixture was cooled down to 273 K in an ice bath. Methyl hydrazine (11.1 ml) was added slowly with mechanical stirring. A solution of CS2 (12 ml) was added dropwise from a burette with constant stirring over a period of 1 h. During the addition of CS2, the temperature of the reaction mixture was not allowed to rise above 279 K. A yellow colour was obtained. After adding carbon disulfide, benzyl chloride (25 ml) was added from a burette dropwise with vigorous mechanical stirring. After complete addition, the mixture was stirred for further 15 min, whereupon shining crystals appeared. The product was separated by filtration, washed with water, recrystallized from ethanol and dried in a vacuum desiccator over silica gel. Yield: 14.20 g. m.p. 373–374 K.
Step 2. Synthesis of the title molecule. A hot solution of furan-2-carbaldehyde (10 mmol) in absolute ethanol (40 ml) was mixed with a hot solution of N-methyl-S-benzyldithiocarbazate (10 mmol) in 40 ml of the same solvent. The mixture was refluxed for 6 h on a water bath. After reducing the volume, an off white product appeared which was filtered off. This product was washed with ethanol several times and dried in a vacuum desiccator over silica gel. Yield: 1.65 g. m.p. 432–434 K.
Step 3. Crystallization. The product was dissolved in ethanol to which half volume of petroleum ether was added (2:1 v/v, 10 ml ethanol and 5 ml petroleum ether). The solution was left for several days after which crystals of the title compound deposited.
All H atoms were placed in idealized positions and allowed to ride on their parent C atoms, with C—H bond lengths fixed to 0.93 (aromatic CH), 0.97 (methylene CH2) or 0.96 Å (methyl CH3). Displacement parameters were taken as Uiso(H) = 1.5Ueq(C9) for the methyl group and Uiso(H) = 1.2Ueq(carrier C) otherwise. The furan ring exhibits rotational disorder over two orientations. The occupancies for all sites were fixed to 0.5, since the refined occupancy for each part was very close to that distribution. In order to approximate the expected geometry for both furan groups, their bond lengths were restrained to be identical, with an effective standard deviation of 0.01 Å (command SAME in SHELXL97; Sheldrick, 2008).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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).The molecular structure of the title molecule, showing displacement ellipsoids at the 50% probability level for non-H atoms. Crystal packing for the title compound viewed along a. |
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 |
C14H14N2OS2 | V = 1442.09 (14) Å3 |
Mr = 290.39 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.0415 (3) Å | µ = 0.36 mm−1 |
b = 20.4840 (11) Å | T = 298 K |
c = 11.8959 (7) Å | 0.5 × 0.5 × 0.3 mm |
β = 101.601 (5)° |
Oxford Diffraction Gemini CCD S Ultra diffractometer | 3361 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 2393 reflections with I > 2σ(I) |
Tmin = 0.850, Tmax = 0.897 | Rint = 0.033 |
21725 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 12 restraints |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.16 e Å−3 |
3361 reflections | Δρmin = −0.17 e Å−3 |
219 parameters |
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 |
Table 1. Cg is the centroid of the phenyl ring |
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 |
Symmetry codes: (i) −x−1, −y, −z+1; (ii) −x+1, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C14H14N2OS2 |
Mr | 290.39 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 6.0415 (3), 20.4840 (11), 11.8959 (7) |
β (°) | 101.601 (5) |
V (Å3) | 1442.09 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.5 × 0.5 × 0.3 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini CCD S Ultra diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.850, 0.897 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21725, 3361, 2393 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.090, 1.06 |
No. of reflections | 3361 |
No. of parameters | 219 |
No. of restraints | 12 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.17 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
Table 1. Cg is the centroid of the phenyl ring |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7B···Cgi | 0.969 | 2.88 | 3.560 (2) | 128 |
C13—H13A···Cgii | 0.932 | 2.80 | 3.62 (2) | 149 |
Symmetry codes: (i) −x−1, −y, −z+1; (ii) −x+1, −y, −z+2. |
Acknowledgements
The authors acknowledge the University Grants Commission (UGC), Bangladesh, for the award of a fellowship to BG and thank the Third World Academy of Sciences (TWAS), Trieste, Italy, for awarding a TWAS–UNESCO Associateship to TGR. They are also grateful to ANPCyT for a grant (PME–2006–01113) and especially to R. Baggio for his helpful suggestions.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As a continuation of systematic studies into the synthesis, characterization and biological activities of substituted Schiff base ligands and their metal complexes (Ganguly et al., 2011; Hazari et al., 2012), the present investigation is an attempt to prepare complexes of vanadium(IV) and molybdenum(VI) with the title Schiff base ligand, benzyl 2-methyl-3-[(E)-(furan-2-yl)-methylidene]dithiocarbazate. Crystals of the title compound were isolated (see Experimental) and characterized crystallographically.
In the title compound (Fig. 1), C14H14N2OS2, the furan ring exhibits rotational disorder over two orientations, with an occupancy of 0.5 for each orientation. The thione S atom and methyl group are syn and the conformation about the imine N2═C10 bond [1.281 (2) Å] is E, in agreement with similar structures (Hazari et al., 2012).
The eight atoms of the central residue (S1, S2, N1, N2, C7, C8, C9 and C10) are co-planar having a r.m.s. deviation for the fitted atoms of 0.002 Å. The maximum deviations from this plane are 0.043 (2) Å for the N2 atom and -0.033 (3) Å for the N1 atom. The molecule is twisted, the dihedral angles between the C4N2S2 residue and the pendent 2-furanyl and phenyl rings being 14.8 (6) [or 8.22 (6) for the disordered part of the furanyl] and 73.65 (9)° respectively, as found in a similar compound (Shan et al., 2008).
In the crystal, molecules assemble into a three-dimensional architecture by π ··· π stacking between 2-furanyl rings [Cg1···Cg1iii = 4.467 (7) Å, Cg1 is the centroid of ring O1, C11, C12, C13, C14; symmetry code: iii 4-x, -y, 2-z], and C–H ··· π interactions, involving the phenyl ring as acceptor (see Table 1 and Fig. 2).