Crystal structure of (E)-2-[1-(1,3-benzodioxol-5-yl)ethyl­idene]-N-ethyl­hydra­zine-1-carbo­thio­amide

Oliveira, A.B. de; Lira de Farias, R.; Näther, C.; Jess, I.

doi:10.1107/S2056989015003837

organic compounds

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ISSN: 2056-9890

Volume 71| Part 3| March 2015| Pages o208-o209

doi:10.1107/S2056989015003837

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Crystal structure of (E)-2-[1-(1,3-benzodioxol-5-yl)ethylidene]-N-ethylhydrazine-1-carbothioamide

Adriano Bof de Oliveira,^a ^* Renan Lira de Farias,^a Christian Näther ^b and Inke Jess ^b

^aDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus, 49100-000 São Cristóvão-SE, Brazil, and ^bInstitut für Anorganische Chemie, Christian-Albrechts-Universität zu Kiel, Max-Eyth Strasse 2, D-24118 Kiel, Germany
^*Correspondence e-mail: adriano@daad-alumni.de

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 12 February 2015; accepted 24 February 2015; online 28 February 2015)

In the title compound, C₁₂H₁₅N₃O₂S, the 1,3-benzdioxole fragment is nearly planar [the maximum deviation being 0.0515 (14) Å], the N—N—C(=S)—N fragment is also nearly planar [the maximum deviation being 0.0480 (10) Å], and the dihedral angle between their mean planes is 23.49 (10)°. In the crystal, molecules are linked by pairs of N—H⋯S hydrogen bonds, forming inversion dimers. The dimers are stacked along the a axis with neighbouring columns having the same direction; however, the molecules show different orientations leading to a centrosymmetric arrangement. In the crystal, the methylene group of the ethyl substituent and the terminal methyl H atoms are disordered over two sets of sites and were refined using a split model with an occupancy ratio of 0.5:0.5.

Keywords: crystal structure; thiosemicarbazone; benzo[d][1,3]dioxole; N—H⋯S hydrogen bonds.

CCDC reference: 1051034

1. Related literature

For one of the first reports of the synthesis of thiosemicarbazone derivatives, see: Freund & Schander (1902 ). For one of the first reports of 3′,4′-(methylenedioxy)acetophenone extraction from the South American Aniba rosaeodora tree, see: Mors et al. (1957 ). For the crystal structures of two derivatives of the title compound, see: Oliveira et al. (2013 , 2015 ).

2. Experimental

2.1. Crystal data

C₁₂H₁₅N₃O₂S
M_r = 265.33
Triclinic, $[P \overline 1]$
a = 5.7207 (3) Å
b = 10.6225 (6) Å
c = 10.8103 (6) Å
α = 83.908 (5)°
β = 79.913 (5)°
γ = 87.029 (5)°
V = 642.74 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 250 K
0.15 × 0.15 × 0.10 mm

2.2. Data collection

Stoe IPDS-1 diffractometer
9389 measured reflections
2811 independent reflections
2288 reflections with I > 2σ(I)
R_int = 0.042

2.3. Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.116
S = 1.03
2811 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.28 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
N2—H1N2⋯S1ⁱ	0.87	2.72	3.5842 (14)	175
Symmetry code: (i) -x, -y+1, -z.

Data collection: X-AREA (Stoe & Cie, 2008 ); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013-2 (Sheldrick, 2015 ); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1051034

Crystal structure: contains datablocks I, publication_text. DOI: 10.1107/S2056989015003837/xu5837sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015003837/xu5837Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015003837/xu5837Isup3.cml

checkCIF report

Structural commentary top

Concerning our interest and on going research on thiosemicarbazone derivatives from natural products, we report herein the synthesis and crystal structure of 1-(2H-1,3-benzodioxol-5-yl)ethanone 4-ethylthiosemicarbazide. The carbonylated precursor is a secondary metabolite from Amazonian Magnoliid trees that belong to the Lauraceae family, the Aniba rosaeodora, (Mors et al., 1957).

The molecular structure of the title compound, which matches the asymmetric unit, is not planar [the mean deviation from planarity for non-H atoms, and excluding the disordered C11/C11' entity, amounts to 0.3794 (17) Å for C5]. The maximum deviation from the mean plane of the non-H atoms of the 1,3-benzodioxole fragment amounts to 0.0515 (14) Å for C7 and for the N1/N2/C10/S1/N3 fragment amounts 0.0480 (10) Å for N2, with the dihedral angle between the planes being 23.49 (10)°.

In the crystal, the molecules are connected by pairs of N2—H1N2···S1 intermolecular hydrogen bonds building dimers. The dimers are stacked along a-axis and although the neighbour columns have the same direction, the dimeric units show different orientations leading to a centrosymmetric structure (Figure 2 and Table 1).

Synthesis and crystallization top

Starting materials are commercially available and were used without further purification. The synthesis of the title compound was adapted from a previously procedure (Freund & Schander, 1902). In a hydrochloric acid catalized reaction, a mixture of 3',4'-(methylenedioxy)acetophenone (10 mmol) and 4-ethyl-3-thiosemicarbazide (10 mmol) in ethanol (80 mL) was refluxed for 4 h. After cooling and filtering, the title compound was obtained. Colourless crystal grown in DMSO by the slow evaporation of the solvent.

Refinement top

The C—H H atoms were positioned with idealized geometry (methyl H atoms were allowed to rotate but not to tip) and refined isotropic with U_iso(H) = 1.2U_eq(C) (1.5 for methyl H atoms) using a riding model with C—H = 0.94 Å for aromatic, C—H = 0.98 Å for methylene and C—H = 0.97 Å for methyl H atoms. The N—H H atoms were located in a difference map and were refined isotropic with varying coordinates in the beginning. Finally, the N—H distances were set to ideal values of 0.87 Å and they were refined isotropic with U_iso(H) = 1.2U_eq(N) using a riding model. The methylene C atom C11 is disordered in two orientations and were refined using a split model with occupancy of 0.5:0.5.

Related literature top

For one of the first reports of the synthesis of thiosemicarbazone derivatives, see: Freund & Schander (1902). For one of the first reports of 3',4'-(methylenedioxy)acetophenone extraction from the South American Aniba rosaeodora tree, see: Mors et al. (1957). For the crystal structures of two derivatives of the title compound, see: Oliveira et al. (2013, 2015).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-RED32 (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013-2 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound with labeling and displacement ellipsoids drawn at the 40% probability level. Disorder is shown with full and open bonds.
	Fig. 2. Crystal structure of the title compound with hydrogen bonding shown as dashed lines (see Table 1 for details). Disordered atoms are not shown for clarity.

(E)-2-[1-(Benzo[d][1,3]dioxol-5-yl)ethylidene]-N-ethylhydrazine-1-carbothioamide top

Crystal data top

C₁₂H₁₅N₃O₂S	Z = 2
M_r = 265.33	F(000) = 280
Triclinic, P1	D_x = 1.371 Mg m⁻³
a = 5.7207 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6225 (6) Å	Cell parameters from 9389 reflections
c = 10.8103 (6) Å	θ = 1.9–27.0°
α = 83.908 (5)°	µ = 0.25 mm⁻¹
β = 79.913 (5)°	T = 250 K
γ = 87.029 (5)°	Parallelepiped, colourless
V = 642.74 (6) Å³	0.15 × 0.15 × 0.10 mm

Data collection top

Stoe IPDS-1 diffractometer	2288 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, Stoe IPDS-1	R_int = 0.042
Graphite monochromator	θ_max = 27.0°, θ_min = 1.9°
ϕ scans	h = −7→7
9389 measured reflections	k = −13→13
2811 independent reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0649P)² + 0.1118P] where P = (F_o² + 2F_c²)/3
2811 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₂H₁₅N₃O₂S	γ = 87.029 (5)°
M_r = 265.33	V = 642.74 (6) Å³
Triclinic, P1	Z = 2
a = 5.7207 (3) Å	Mo Kα radiation
b = 10.6225 (6) Å	µ = 0.25 mm⁻¹
c = 10.8103 (6) Å	T = 250 K
α = 83.908 (5)°	0.15 × 0.15 × 0.10 mm
β = 79.913 (5)°

Data collection top

Stoe IPDS-1 diffractometer	2288 reflections with I > 2σ(I)
9389 measured reflections	R_int = 0.042
2811 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.03	Δρ_max = 0.28 e Å⁻³
2811 reflections	Δρ_min = −0.23 e Å⁻³
173 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	Occ. (<1)
C1	0.7435 (3)	0.18956 (14)	0.16339 (15)	0.0407 (3)
C2	0.8619 (3)	0.24715 (14)	0.24537 (15)	0.0428 (3)
H2	0.8352	0.3334	0.2575	0.051*
C3	1.0167 (3)	0.17309 (16)	0.30646 (16)	0.0457 (4)
C4	1.0618 (3)	0.04644 (16)	0.28893 (17)	0.0516 (4)
C5	0.9543 (4)	−0.01187 (16)	0.20857 (19)	0.0581 (5)
H5	0.9863	−0.0977	0.1962	0.070*
C6	0.7937 (3)	0.06224 (16)	0.14522 (17)	0.0515 (4)
H6	0.7174	0.0250	0.0887	0.062*
O1	1.1441 (2)	0.20752 (13)	0.39317 (13)	0.0621 (4)
C7	1.2882 (3)	0.0980 (2)	0.4229 (2)	0.0615 (5)
H7A	1.4562	0.1148	0.3917	0.074*
H7B	1.2668	0.0771	0.5146	0.074*
O2	1.2191 (3)	−0.00457 (13)	0.36476 (15)	0.0698 (4)
C8	0.5558 (3)	0.26302 (14)	0.10543 (15)	0.0407 (3)
C9	0.4637 (3)	0.21798 (17)	−0.00254 (18)	0.0541 (4)
H9A	0.3116	0.1794	0.0280	0.081*
H9B	0.5755	0.1560	−0.0415	0.081*
H9C	0.4440	0.2892	−0.0643	0.081*
N1	0.4771 (2)	0.36261 (12)	0.15902 (13)	0.0420 (3)
N2	0.2949 (2)	0.43540 (12)	0.11811 (13)	0.0432 (3)
H1N2	0.2234	0.4229	0.0560	0.052*
C10	0.2019 (3)	0.53176 (15)	0.18658 (16)	0.0461 (4)
S1	−0.03625 (8)	0.61725 (4)	0.15015 (5)	0.05451 (17)
N3	0.3122 (3)	0.55269 (18)	0.27906 (18)	0.0732 (5)
H1N3	0.4362	0.5027	0.2843	0.088*
C11	0.2171 (16)	0.6290 (8)	0.3858 (8)	0.071 (2)	0.5
H11A	0.1138	0.6987	0.3576	0.085*	0.5
H11B	0.1232	0.5758	0.4544	0.085*	0.5
C11'	0.2731 (18)	0.6716 (7)	0.3447 (8)	0.0675 (19)	0.5
H11C	0.2989	0.7447	0.2812	0.081*	0.5
H11D	0.1073	0.6766	0.3872	0.081*	0.5
C12	0.4155 (6)	0.6790 (3)	0.4304 (3)	0.1149 (12)
H12A	0.5616	0.6353	0.3959	0.172*	0.5
H12B	0.3914	0.6663	0.5219	0.172*	0.5
H12C	0.4259	0.7689	0.4032	0.172*	0.5
H12D	0.4978	0.5980	0.4444	0.172*	0.5
H12E	0.3205	0.7007	0.5092	0.172*	0.5
H12F	0.5307	0.7438	0.3993	0.172*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0423 (7)	0.0354 (7)	0.0438 (8)	0.0004 (6)	−0.0029 (6)	−0.0089 (6)
C2	0.0447 (8)	0.0345 (7)	0.0491 (8)	−0.0006 (6)	−0.0058 (6)	−0.0077 (6)
C3	0.0450 (8)	0.0449 (8)	0.0467 (8)	−0.0031 (6)	−0.0063 (6)	−0.0043 (6)
C4	0.0492 (9)	0.0433 (9)	0.0588 (10)	0.0060 (7)	−0.0064 (7)	0.0028 (7)
C5	0.0666 (11)	0.0355 (8)	0.0716 (12)	0.0095 (7)	−0.0103 (9)	−0.0106 (8)
C6	0.0577 (10)	0.0395 (8)	0.0594 (10)	0.0034 (7)	−0.0105 (8)	−0.0161 (7)
O1	0.0644 (8)	0.0599 (8)	0.0684 (8)	0.0018 (6)	−0.0293 (7)	−0.0074 (6)
C7	0.0524 (10)	0.0694 (12)	0.0607 (11)	0.0010 (9)	−0.0142 (8)	0.0083 (9)
O2	0.0699 (9)	0.0565 (8)	0.0853 (10)	0.0114 (6)	−0.0292 (7)	0.0024 (7)
C8	0.0417 (7)	0.0357 (7)	0.0449 (8)	−0.0012 (6)	−0.0050 (6)	−0.0095 (6)
C9	0.0538 (9)	0.0522 (10)	0.0617 (10)	0.0070 (7)	−0.0156 (8)	−0.0245 (8)
N1	0.0417 (6)	0.0370 (6)	0.0485 (7)	0.0033 (5)	−0.0086 (5)	−0.0108 (5)
N2	0.0430 (7)	0.0398 (7)	0.0501 (7)	0.0048 (5)	−0.0128 (5)	−0.0150 (5)
C10	0.0464 (8)	0.0403 (8)	0.0539 (9)	0.0033 (6)	−0.0106 (7)	−0.0150 (7)
S1	0.0481 (2)	0.0521 (3)	0.0700 (3)	0.01332 (18)	−0.02210 (19)	−0.0241 (2)
N3	0.0788 (11)	0.0749 (11)	0.0815 (11)	0.0404 (9)	−0.0444 (9)	−0.0480 (9)
C11	0.070 (4)	0.073 (5)	0.081 (6)	0.027 (4)	−0.029 (4)	−0.046 (4)
C11'	0.087 (5)	0.057 (4)	0.068 (5)	0.027 (3)	−0.032 (4)	−0.033 (3)
C12	0.109 (2)	0.133 (3)	0.122 (2)	0.029 (2)	−0.0365 (19)	−0.089 (2)

Geometric parameters (Å, º) top

C1—C6	1.395 (2)	N1—N2	1.3730 (18)
C1—C2	1.410 (2)	N2—C10	1.358 (2)
C1—C8	1.483 (2)	N2—H1N2	0.8699
C2—C3	1.364 (2)	C10—N3	1.315 (2)
C2—H2	0.9400	C10—S1	1.6792 (17)
C3—O1	1.372 (2)	N3—C11	1.489 (9)
C3—C4	1.383 (2)	N3—C11'	1.501 (9)
C4—C5	1.363 (3)	N3—H1N3	0.8700
C4—O2	1.375 (2)	C11—C12	1.453 (10)
C5—C6	1.401 (3)	C11—H11A	0.9800
C5—H5	0.9400	C11—H11B	0.9800
C6—H6	0.9400	C11'—C12	1.347 (10)
O1—C7	1.432 (2)	C11'—H11C	0.9800
C7—O2	1.420 (3)	C11'—H11D	0.9800
C7—H7A	0.9800	C12—H12A	0.9700
C7—H7B	0.9800	C12—H12B	0.9700
C8—N1	1.2832 (19)	C12—H12C	0.9700
C8—C9	1.493 (2)	C12—H12D	0.9700
C9—H9A	0.9700	C12—H12E	0.9700
C9—H9B	0.9700	C12—H12F	0.9700
C9—H9C	0.9700

C6—C1—C2	119.34 (15)	C10—N2—N1	117.50 (13)
C6—C1—C8	121.30 (15)	C10—N2—H1N2	115.4
C2—C1—C8	119.22 (13)	N1—N2—H1N2	126.9
C3—C2—C1	117.54 (14)	N3—C10—N2	115.66 (15)
C3—C2—H2	121.2	N3—C10—S1	123.92 (12)
C1—C2—H2	121.2	N2—C10—S1	120.41 (13)
C2—C3—O1	127.54 (15)	C10—N3—C11	126.2 (4)
C2—C3—C4	122.40 (16)	C10—N3—C11'	123.1 (4)
O1—C3—C4	110.05 (15)	C10—N3—H1N3	113.3
C5—C4—O2	128.69 (16)	C11—N3—H1N3	119.0
C5—C4—C3	121.73 (16)	C11'—N3—H1N3	121.5
O2—C4—C3	109.57 (17)	C12—C11—N3	108.7 (6)
C4—C5—C6	116.86 (15)	C12—C11—H11A	110.0
C4—C5—H5	121.6	N3—C11—H11A	110.0
C6—C5—H5	121.6	C12—C11—H11B	110.0
C1—C6—C5	122.10 (17)	N3—C11—H11B	110.0
C1—C6—H6	118.9	H11A—C11—H11B	108.3
C5—C6—H6	118.9	C12—C11'—N3	114.0 (6)
C3—O1—C7	105.38 (14)	C12—C11'—H11C	108.7
O2—C7—O1	108.49 (15)	N3—C11'—H11C	108.7
O2—C7—H7A	110.0	C12—C11'—H11D	108.7
O1—C7—H7A	110.0	N3—C11'—H11D	108.7
O2—C7—H7B	110.0	H11C—C11'—H11D	107.6
O1—C7—H7B	110.0	C11—C12—H12A	109.5
H7A—C7—H7B	108.4	C11—C12—H12B	109.5
C4—O2—C7	105.90 (14)	H12A—C12—H12B	109.5
N1—C8—C1	114.42 (14)	C11—C12—H12C	109.5
N1—C8—C9	124.48 (15)	H12A—C12—H12C	109.5
C1—C8—C9	121.04 (13)	H12B—C12—H12C	109.5
C8—C9—H9A	109.5	C11'—C12—H12D	109.5
C8—C9—H9B	109.5	C11'—C12—H12E	109.5
H9A—C9—H9B	109.5	H12D—C12—H12E	109.5
C8—C9—H9C	109.5	C11'—C12—H12F	109.5
H9A—C9—H9C	109.5	H12D—C12—H12F	109.5
H9B—C9—H9C	109.5	H12E—C12—H12F	109.5
C8—N1—N2	120.07 (14)

C6—C1—C2—C3	−1.9 (2)	C6—C1—C8—N1	159.25 (15)
C8—C1—C2—C3	173.75 (14)	C2—C1—C8—N1	−16.3 (2)
C1—C2—C3—O1	−177.54 (15)	C6—C1—C8—C9	−18.1 (2)
C1—C2—C3—C4	1.0 (2)	C2—C1—C8—C9	166.30 (15)
C2—C3—C4—C5	0.3 (3)	C1—C8—N1—N2	−176.84 (12)
O1—C3—C4—C5	179.06 (16)	C9—C8—N1—N2	0.4 (2)
C2—C3—C4—O2	−178.38 (15)	C8—N1—N2—C10	173.15 (14)
O1—C3—C4—O2	0.34 (19)	N1—N2—C10—N3	6.2 (2)
O2—C4—C5—C6	177.85 (17)	N1—N2—C10—S1	−174.75 (11)
C3—C4—C5—C6	−0.6 (3)	N2—C10—N3—C11	−164.2 (4)
C2—C1—C6—C5	1.7 (3)	S1—C10—N3—C11	16.8 (5)
C8—C1—C6—C5	−173.86 (16)	N2—C10—N3—C11'	165.3 (4)
C4—C5—C6—C1	−0.4 (3)	S1—C10—N3—C11'	−13.8 (5)
C2—C3—O1—C7	−176.90 (16)	C10—N3—C11—C12	−153.3 (4)
C4—C3—O1—C7	4.46 (18)	C11'—N3—C11—C12	−61.3 (15)
C3—O1—C7—O2	−7.55 (19)	C10—N3—C11'—C12	−175.3 (4)
C5—C4—O2—C7	176.35 (19)	C11—N3—C11'—C12	79.0 (15)
C3—C4—O2—C7	−5.04 (19)	N3—C11'—C12—C11	−73.0 (13)
O1—C7—O2—C4	7.8 (2)	N3—C11—C12—C11'	68.3 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1ⁱ	0.87	2.72	3.5842 (14)	175

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1ⁱ	0.87	2.72	3.5842 (14)	175.2

Symmetry code: (i) −x, −y+1, −z.

Acknowledgements

We gratefully acknowledge financial support by the State of Schleswig–Holstein, Germany, and Professor Dr Wolfgang Bensch for access to his experimental facilities. We acknowledge also the financial support by FAPITEC/SE/FUNTEC/CNPq through the PPP Program 04/2011.

References

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Volume 71| Part 3| March 2015| Pages o208-o209

doi:10.1107/S2056989015003837

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

Crystal structure of (E)-2-[1-(1,3-benzodioxol-5-yl)ethyl­­idene]-N-ethyl­hydra­zine-1-carbo­thio­amide

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (E)-2-[1-(1,3-benzodioxol-5-yl)ethylidene]-N-ethylhydrazine-1-carbothioamide