Methyl 3-(2-hy-droxy-benzyl-idene)-2-methyl-dithio-carbazate.

In the title compound, C(10)H(12)N(2)OS(2), the thione and S-methyl groups are syn. An intra-molecular bifurcated O-H⋯(S,N) hydrogen bond occurs.

Related literature

For the biological activity of sulfur-ligand compounds, see: French & Blang (1965 ▶); Ali & Livingstone (1974 ▶); Ali et al. (1995 ▶); Hazari et al. (1999 ▶, 2002 ▶). For the synthesis and characterization of sulfur–nitro­gen-containing ligands, see: Hazari et al. (2002 ▶, 2006 ▶). For a related structure, see: Hazari et al. (2012 ▶).

Experimental

Crystal data

C10H12N2OS2

M = 240.34

Monoclinic,

a = 11.3561 (16) Å

b = 8.9033 (13) Å

c = 11.5045 (16) Å

β = 91.411 (13)°

V = 1162.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 298 K

0.35 × 0.30 × 0.22 mm

Data collection

Oxford Diffraction Gemini CCD S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.859, T max = 0.917

16680 measured reflections

2833 independent reflections

2039 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.171

S = 1.05

2833 reflections

144 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201731X/qm2064sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201731X/qm2064Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201731X/qm2064Isup3.cml

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

C10H12N2OS2	F(000) = 504
Mr = 240.34	Dx = 1.373 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 0 reflections
a = 11.3561 (16) Å	θ = 4.0–29.1°
b = 8.9033 (13) Å	µ = 0.43 mm−1
c = 11.5045 (16) Å	T = 298 K
β = 91.411 (13)°	Prism, colourless
V = 1162.8 (3) Å3	0.35 × 0.30 × 0.22 mm
Z = 4

Oxford Diffraction Gemini CCD S Ultra diffractometer	2039 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω scans	θmax = 29.1°, θmin = 4.0°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −14→15
Tmin = 0.859, Tmax = 0.917	k = −11→11
16680 measured reflections	l = −14→15
2833 independent reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0801P)2 + 0.6976P] where P = (Fo2 + 2Fc2)/3
2833 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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
S2	0.74513 (6)	0.31081 (8)	0.59687 (6)	0.0526 (2)
S1	0.88032 (7)	0.14078 (11)	0.78107 (8)	0.0705 (3)
O1	0.47228 (19)	0.2727 (3)	0.4609 (2)	0.0610 (6)
N1	0.56325 (18)	0.1339 (2)	0.64913 (17)	0.0411 (5)
N2	0.65614 (19)	0.0963 (2)	0.72163 (18)	0.0447 (5)
C6	0.3631 (2)	0.1080 (3)	0.5859 (2)	0.0434 (5)
C7	0.4625 (2)	0.0705 (3)	0.6613 (2)	0.0437 (6)
C1	0.3700 (2)	0.2072 (3)	0.4911 (2)	0.0444 (6)
C8	0.6446 (3)	−0.0200 (3)	0.8097 (2)	0.0582 (7)
H8A	0.5658	−0.0592	0.8067	0.087*
H8B	0.6609	0.0221	0.8852	0.087*
H8C	0.6994	−0.0995	0.7952	0.087*
C5	0.2542 (2)	0.0437 (4)	0.6081 (3)	0.0591 (7)
H5	0.2485	−0.024	0.6692	0.071*
C9	0.7587 (2)	0.1735 (3)	0.7057 (2)	0.0449 (6)
C2	0.2700 (3)	0.2389 (4)	0.4249 (3)	0.0578 (7)
H2	0.2745	0.3047	0.3624	0.069*
C3	0.1633 (3)	0.1742 (4)	0.4505 (3)	0.0681 (9)
H3	0.0966	0.1964	0.4052	0.082*
C10	0.8904 (3)	0.3907 (4)	0.5977 (3)	0.0668 (8)
H10A	0.8935	0.469	0.5405	0.1*
H10B	0.9466	0.3141	0.5798	0.1*
H10C	0.9087	0.4316	0.6732	0.1*
C4	0.1553 (3)	0.0767 (4)	0.5430 (3)	0.0725 (9)
H4	0.0833	0.0339	0.561	0.087*
H7	0.444 (3)	0.007 (4)	0.717 (3)	0.082 (11)*
H1O	0.527 (4)	0.253 (5)	0.518 (4)	0.087 (12)*

	U11	U22	U33	U12	U13	U23
S2	0.0478 (4)	0.0548 (4)	0.0548 (4)	−0.0099 (3)	−0.0043 (3)	0.0076 (3)
S1	0.0517 (5)	0.0886 (6)	0.0702 (5)	0.0089 (4)	−0.0151 (4)	0.0073 (4)
O1	0.0498 (12)	0.0718 (13)	0.0614 (12)	−0.0079 (10)	0.0019 (10)	0.0231 (11)
N1	0.0439 (11)	0.0376 (10)	0.0420 (10)	0.0021 (8)	0.0009 (8)	0.0019 (8)
N2	0.0446 (11)	0.0443 (11)	0.0449 (11)	0.0052 (9)	−0.0033 (9)	0.0064 (9)
C6	0.0461 (13)	0.0399 (12)	0.0444 (12)	−0.0027 (10)	0.0045 (10)	−0.0078 (10)
C7	0.0509 (14)	0.0382 (12)	0.0424 (13)	−0.0036 (10)	0.0073 (10)	0.0003 (10)
C1	0.0461 (14)	0.0414 (12)	0.0458 (13)	0.0007 (10)	0.0044 (10)	−0.0043 (10)
C8	0.0687 (19)	0.0524 (15)	0.0535 (15)	0.0052 (13)	0.0018 (13)	0.0158 (12)
C5	0.0512 (16)	0.0632 (18)	0.0629 (17)	−0.0167 (13)	0.0031 (13)	0.0018 (14)
C9	0.0455 (14)	0.0455 (13)	0.0438 (13)	0.0070 (10)	0.0016 (10)	−0.0048 (10)
C2	0.0597 (17)	0.0575 (16)	0.0558 (16)	0.0069 (13)	−0.0035 (13)	−0.0027 (13)
C3	0.0525 (18)	0.079 (2)	0.072 (2)	0.0066 (15)	−0.0142 (15)	−0.0106 (17)
C10	0.0519 (17)	0.076 (2)	0.073 (2)	−0.0139 (15)	0.0075 (15)	0.0017 (16)
C4	0.0472 (17)	0.088 (2)	0.083 (2)	−0.0162 (16)	−0.0050 (15)	−0.0018 (19)

S2—C9	1.754 (3)	C8—H8A	0.96
S2—C10	1.796 (3)	C8—H8B	0.96
S1—C9	1.639 (3)	C8—H8C	0.96
O1—C1	1.353 (3)	C5—C4	1.366 (5)
O1—H1O	0.91 (4)	C5—H5	0.93
N1—C7	1.286 (3)	C2—C3	1.380 (5)
N1—N2	1.370 (3)	C2—H2	0.93
N2—C9	1.368 (3)	C3—C4	1.378 (5)
N2—C8	1.457 (3)	C3—H3	0.93
C6—C5	1.392 (4)	C10—H10A	0.96
C6—C1	1.408 (4)	C10—H10B	0.96
C6—C7	1.446 (4)	C10—H10C	0.96
C7—H7	0.89 (4)	C4—H4	0.93
C1—C2	1.381 (4)
C9—S2—C10	102.00 (15)	C4—C5—C6	122.2 (3)
C1—O1—H1O	108 (3)	C4—C5—H5	118.9
C7—N1—N2	120.0 (2)	C6—C5—H5	118.9
C9—N2—N1	116.2 (2)	N2—C9—S1	123.3 (2)
C9—N2—C8	122.8 (2)	N2—C9—S2	112.69 (19)
N1—N2—C8	121.0 (2)	S1—C9—S2	124.01 (17)
C5—C6—C1	117.8 (3)	C3—C2—C1	120.8 (3)
C5—C6—C7	118.7 (2)	C3—C2—H2	119.6
C1—C6—C7	123.5 (2)	C1—C2—H2	119.6
N1—C7—C6	121.1 (2)	C4—C3—C2	120.2 (3)
N1—C7—H7	126 (2)	C4—C3—H3	119.9
C6—C7—H7	113 (2)	C2—C3—H3	119.9
O1—C1—C2	118.1 (3)	S2—C10—H10A	109.5
O1—C1—C6	122.3 (2)	S2—C10—H10B	109.5
C2—C1—C6	119.7 (3)	H10A—C10—H10B	109.5
N2—C8—H8A	109.5	S2—C10—H10C	109.5
N2—C8—H8B	109.5	H10A—C10—H10C	109.5
H8A—C8—H8B	109.5	H10B—C10—H10C	109.5
N2—C8—H8C	109.5	C5—C4—C3	119.4 (3)
H8A—C8—H8C	109.5	C5—C4—H4	120.3
H8B—C8—H8C	109.5	C3—C4—H4	120.3

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···S2	0.91 (5)	2.67 (5)	3.453 (2)	145 (4)
O1—H1O···N1	0.91 (5)	1.88 (5)	2.678 (3)	145 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯S2	0.91 (5)	2.67 (5)	3.453 (2)	145 (4)
O1—H1O⋯N1	0.91 (5)	1.88 (5)	2.678 (3)	145 (4)