1-(2H-1,3-Benzodioxol-5-yl)ethanone thio-semicarbazone.

In the title compound, C10H11N3O2S, the 1,3-benzodioxole and hydrazinecarbothio-amide fragments are nearly planar [(mean deviations from planarity for non-H atoms of 0.0325 (12) Å and 0.0707 (10) Å, respectively] and subtend a dihedral angle of 29.06 (5)°. In the crystal, mol-ecules are linked by pairs of almost linear N-H⋯S hydrogen bonds, forming inversion dimers. These dimers are additionally connected by weaker and strongly bent N-H⋯S inter-actions into chains along [101]. There is one additional weak N-H⋯O contact which, if considered as an inter-action, leads to the formation of a three-dimensional network.

Related literature

For the adapted synthesis of the title compound, see: de Oliveira et al. (2012 ▶). For the pharmacological activity of 3′,4′-(methyl­enedi­oxy)acetophenone thio­simecarbazone derivatives, see: Silva et al. (1998 ▶).

Experimental

Crystal data

C10H11N3O2S

M = 237.28

Monoclinic,

a = 6.1423 (12) Å

b = 26.065 (5) Å

c = 7.1289 (14) Å

β = 109.07 (3)°

V = 1078.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 200 K

0.3 × 0.2 × 0.2 mm

Data collection

Stoe IPDS-1 diffractometer

12310 measured reflections

2315 independent reflections

2018 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.107

S = 1.04

2315 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.32 e Å−3

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: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2011 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008398/qk2055sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008398/qk2055Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008398/qk2055Isup3.cml

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

C10H11N3O2S	F(000) = 496
Mr = 237.28	Dx = 1.461 Mg m−3
Monoclinic, P21/c	Melting point: 460.2 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.1423 (12) Å	Cell parameters from 8000 reflections
b = 26.065 (5) Å	θ = 3–27.9°
c = 7.1289 (14) Å	µ = 0.29 mm−1
β = 109.07 (3)°	T = 200 K
V = 1078.7 (4) Å3	Block, yellow
Z = 4	0.3 × 0.2 × 0.2 mm

Stoe IPDS-1 diffractometer	2018 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 27.0°, θmin = 3.1°
φ scans	h = −7→7
12310 measured reflections	k = −33→33
2315 independent reflections	l = −9→9

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0692P)2 + 0.2915P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2315 reflections	Δρmax = 0.29 e Å−3
147 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.047 (8)

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
N1	0.2311 (2)	0.43475 (5)	0.0548 (2)	0.0326 (3)
H1N1	0.2765	0.4032	0.0431	0.049*
H2N1	0.0917	0.4461	−0.0094	0.049*
C1	0.3775 (3)	0.46661 (5)	0.1778 (2)	0.0229 (3)
S1	0.31425 (7)	0.528178 (13)	0.21371 (6)	0.03093 (17)
N2	0.5891 (2)	0.44885 (4)	0.28111 (18)	0.0252 (3)
H1N2	0.6685	0.4673	0.3840	0.030*
N3	0.6401 (2)	0.39750 (4)	0.26964 (18)	0.0230 (3)
C2	0.8498 (2)	0.38377 (5)	0.3628 (2)	0.0205 (3)
C3	1.0366 (3)	0.42034 (6)	0.4726 (3)	0.0332 (4)
H3A	1.0430	0.4489	0.3850	0.050*
H3B	1.1849	0.4024	0.5151	0.050*
H3C	1.0039	0.4336	0.5892	0.050*
C4	0.8967 (2)	0.32787 (5)	0.3605 (2)	0.0201 (3)
C5	1.1206 (3)	0.30922 (6)	0.4082 (2)	0.0276 (3)
H5	1.2450	0.3329	0.4394	0.033*
C6	1.1679 (3)	0.25646 (6)	0.4115 (3)	0.0320 (4)
H6	1.3209	0.2440	0.4421	0.038*
C7	0.9848 (3)	0.22397 (5)	0.3689 (2)	0.0250 (3)
O1	0.9848 (2)	0.17122 (4)	0.36822 (19)	0.0362 (3)
C8	0.7485 (3)	0.15623 (6)	0.3202 (3)	0.0329 (4)
H8A	0.7026	0.1345	0.1997	0.039*
H8B	0.7267	0.1362	0.4308	0.039*
O2	0.6109 (2)	0.20154 (4)	0.2866 (2)	0.0409 (3)
C9	0.7615 (3)	0.24196 (5)	0.3209 (2)	0.0241 (3)
C10	0.7108 (3)	0.29321 (5)	0.3141 (2)	0.0242 (3)
H10	0.5562	0.3049	0.2795	0.029*

	U11	U22	U33	U12	U13	U23
N1	0.0320 (7)	0.0199 (6)	0.0367 (8)	0.0067 (5)	−0.0014 (6)	−0.0073 (5)
C1	0.0269 (7)	0.0175 (6)	0.0227 (7)	0.0036 (5)	0.0060 (6)	0.0011 (5)
S1	0.0335 (3)	0.0145 (2)	0.0383 (3)	0.00688 (13)	0.00280 (18)	−0.00235 (13)
N2	0.0285 (7)	0.0133 (6)	0.0287 (7)	0.0050 (4)	0.0022 (5)	−0.0034 (4)
N3	0.0278 (6)	0.0128 (5)	0.0255 (6)	0.0044 (4)	0.0049 (5)	−0.0015 (4)
C2	0.0231 (7)	0.0162 (6)	0.0226 (7)	0.0011 (5)	0.0079 (6)	−0.0007 (5)
C3	0.0258 (8)	0.0250 (7)	0.0475 (10)	−0.0039 (6)	0.0101 (7)	−0.0084 (6)
C4	0.0220 (7)	0.0168 (6)	0.0204 (6)	0.0039 (5)	0.0056 (5)	0.0008 (5)
C5	0.0219 (7)	0.0230 (7)	0.0363 (8)	0.0034 (5)	0.0073 (6)	0.0012 (6)
C6	0.0251 (7)	0.0269 (8)	0.0429 (9)	0.0116 (6)	0.0095 (7)	0.0044 (6)
C7	0.0331 (8)	0.0172 (7)	0.0246 (7)	0.0099 (5)	0.0092 (6)	0.0030 (5)
O1	0.0434 (7)	0.0165 (5)	0.0473 (7)	0.0112 (4)	0.0129 (6)	0.0045 (4)
C8	0.0487 (10)	0.0156 (7)	0.0349 (9)	0.0047 (6)	0.0145 (8)	0.0013 (6)
O2	0.0333 (6)	0.0141 (5)	0.0703 (9)	−0.0002 (4)	0.0100 (6)	−0.0022 (5)
C9	0.0262 (7)	0.0161 (6)	0.0281 (7)	0.0012 (5)	0.0064 (6)	−0.0006 (5)
C10	0.0209 (7)	0.0170 (7)	0.0324 (8)	0.0043 (5)	0.0058 (6)	−0.0006 (5)

N1—C1	1.324 (2)	C4—C10	1.408 (2)
N1—H1N1	0.8802	C5—C6	1.404 (2)
N1—H2N1	0.8800	C5—H5	0.9500
C1—N2	1.3494 (19)	C6—C7	1.361 (2)
C1—S1	1.6901 (14)	C6—H6	0.9500
N2—N3	1.3831 (16)	C7—O1	1.3749 (17)
N2—H1N2	0.8800	C7—C9	1.382 (2)
N3—C2	1.2921 (19)	O1—C8	1.432 (2)
C2—C4	1.4864 (17)	C8—O2	1.4261 (19)
C2—C3	1.500 (2)	C8—H8A	0.9900
C3—H3A	0.9800	C8—H8B	0.9900
C3—H3B	0.9800	O2—C9	1.3704 (18)
C3—H3C	0.9800	C9—C10	1.3690 (19)
C4—C5	1.392 (2)	C10—H10	0.9500
C1—N1—H1N1	118.7	C4—C5—H5	119.0
C1—N1—H2N1	117.9	C6—C5—H5	119.0
H1N1—N1—H2N1	123.4	C7—C6—C5	117.03 (13)
N1—C1—N2	118.10 (12)	C7—C6—H6	121.5
N1—C1—S1	123.79 (12)	C5—C6—H6	121.5
N2—C1—S1	118.11 (11)	C6—C7—O1	128.48 (14)
C1—N2—N3	119.75 (12)	C6—C7—C9	121.67 (13)
C1—N2—H1N2	116.1	O1—C7—C9	109.84 (13)
N3—N2—H1N2	120.3	C7—O1—C8	105.81 (11)
C2—N3—N2	116.40 (12)	O2—C8—O1	108.23 (12)
N3—C2—C4	115.46 (12)	O2—C8—H8A	110.1
N3—C2—C3	123.80 (13)	O1—C8—H8A	110.1
C4—C2—C3	120.72 (13)	O2—C8—H8B	110.1
C2—C3—H3A	109.5	O1—C8—H8B	110.1
C2—C3—H3B	109.5	H8A—C8—H8B	108.4
H3A—C3—H3B	109.5	C9—O2—C8	106.15 (13)
C2—C3—H3C	109.5	C10—C9—O2	127.67 (14)
H3A—C3—H3C	109.5	C10—C9—C7	122.40 (14)
H3B—C3—H3C	109.5	O2—C9—C7	109.93 (12)
C5—C4—C10	119.61 (13)	C9—C10—C4	117.38 (13)
C5—C4—C2	121.26 (13)	C9—C10—H10	121.3
C10—C4—C2	119.12 (12)	C4—C10—H10	121.3
C4—C5—C6	121.91 (14)
N1—C1—N2—N3	−5.7 (2)	C6—C7—O1—C8	178.09 (16)
S1—C1—N2—N3	174.06 (10)	C9—C7—O1—C8	−0.96 (17)
C1—N2—N3—C2	175.99 (13)	C7—O1—C8—O2	1.91 (17)
N2—N3—C2—C4	175.80 (11)	O1—C8—O2—C9	−2.14 (17)
N2—N3—C2—C3	−2.5 (2)	C8—O2—C9—C10	−177.54 (15)
N3—C2—C4—C5	163.15 (13)	C8—O2—C9—C7	1.57 (18)
C3—C2—C4—C5	−18.5 (2)	C6—C7—C9—C10	−0.3 (2)
N3—C2—C4—C10	−18.52 (19)	O1—C7—C9—C10	178.77 (13)
C3—C2—C4—C10	159.82 (14)	C6—C7—C9—O2	−179.51 (15)
C10—C4—C5—C6	0.0 (2)	O1—C7—C9—O2	−0.39 (18)
C2—C4—C5—C6	178.38 (14)	O2—C9—C10—C4	178.34 (15)
C4—C5—C6—C7	−1.0 (2)	C7—C9—C10—C4	−0.7 (2)
C5—C6—C7—O1	−177.77 (15)	C5—C4—C10—C9	0.8 (2)
C5—C6—C7—C9	1.2 (2)	C2—C4—C10—C9	−177.57 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.88	2.66	3.2207 (17)	123
N1—H2N1···S1ii	0.88	2.53	3.4100 (18)	175
N2—H1N2···S1iii	0.88	2.84	3.5048 (15)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.88	2.66	3.2207 (17)	123
N1—H2N1⋯S1ii	0.88	2.53	3.4100 (18)	175
N2—H1N2⋯S1iii	0.88	2.84	3.5048 (15)	134

Symmetry codes: (i) ; (ii) ; (iii) .