2-[(E)-2-Hy-droxy-3-methoxy-benzyl-idene]-N-methyl-hydrazinecarbothio-amide.

In the crystal structure of the title compound, C11H15N3O2S, mol-ecules are linked by pairs of N-H⋯O and O-H⋯S hydrogen, forming inversion dimers. These dimers are linked by N-H⋯S hydrogen bonds, forming double-stranded chains propagating along the b-axis direction. The two C atoms of the end chain of the mol-ecule are disordered over two sets os sites [occupancy ratio 0.574 (9):0.426 (9)].

Related literature

For related structures, see: Joseph et al. (2006 ▶); Ren-Gao Zhao et al.(2008 ▶). For the biological activity of thio­semicarbazone Schiff bases, see: Kasuga et al. (2003 ▶); Murali et al. (2008 ▶, 2009 ▶); Paterson & Donnelly (2011 ▶).

Experimental

Crystal data

C11H15N3O2S

M = 253.32

Monoclinic,

a = 13.251 (6) Å

b = 6.185 (3) Å

c = 16.380 (8) Å

β = 113.153 (7)°

V = 1234.4 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.26 × 0.09 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.936, T max = 0.987

7373 measured reflections

2433 independent reflections

1666 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.180

S = 1.06

2433 reflections

175 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049847/gw2126sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049847/gw2126Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049847/gw2126Isup3.cml

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

C11H15N3O2S	F(000) = 536
Mr = 253.32	Dx = 1.363 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1499 reflections
a = 13.251 (6) Å	θ = 2.6–25.6°
b = 6.185 (3) Å	µ = 0.26 mm−1
c = 16.380 (8) Å	T = 293 K
β = 113.153 (7)°	Rectangular plate like, yellow
V = 1234.4 (11) Å3	0.26 × 0.09 × 0.05 mm
Z = 4

Bruker APEXII CCD diffractometer	2433 independent reflections
Radiation source: fine-focus sealed tube	1666 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 0.3 pixels mm-1	θmax = 26.0°, θmin = 1.7°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −6→7
Tmin = 0.936, Tmax = 0.987	l = −20→20
7373 measured 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0756P)2 + 1.2001P] where P = (Fo2 + 2Fc2)/3
2433 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.46 e Å−3
4 restraints	Δρmin = −0.37 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
S1	0.87523 (8)	0.71851 (17)	0.56230 (8)	0.0642 (4)
O1	0.37812 (19)	0.2015 (4)	0.55013 (16)	0.0483 (6)
O2	0.28859 (18)	−0.1250 (4)	0.60039 (16)	0.0515 (7)
N1	0.7027 (2)	0.2534 (4)	0.60644 (18)	0.0419 (7)
N2	0.7343 (2)	0.4427 (5)	0.5791 (2)	0.0462 (7)
C1	0.5554 (2)	0.0466 (5)	0.61505 (19)	0.0355 (7)
C2	0.4438 (2)	0.0358 (5)	0.59547 (19)	0.0356 (7)
C3	0.3996 (3)	−0.1393 (5)	0.6244 (2)	0.0393 (7)
C4	0.4666 (3)	−0.3038 (6)	0.6715 (2)	0.0457 (8)
C5	0.5792 (3)	−0.2945 (6)	0.6909 (2)	0.0473 (8)
C6	0.6224 (3)	−0.1240 (5)	0.6625 (2)	0.0420 (8)
H6	0.6972	−0.1211	0.6748	0.050*
C7	0.2363 (3)	−0.2905 (7)	0.6292 (3)	0.0617 (11)
H7A	0.2530	−0.4284	0.6107	0.093*
H7B	0.1583	−0.2680	0.6036	0.093*
H7C	0.2621	−0.2871	0.6927	0.093*
C8	0.5999 (3)	0.2336 (5)	0.5868 (2)	0.0386 (7)
C9	0.8392 (3)	0.4794 (6)	0.5909 (2)	0.0491 (9)
N3	0.9010 (4)	0.2968 (11)	0.6089 (5)	0.0524 (17)*	0.574 (9)
H3	0.8756	0.1678	0.5955	0.063*	0.574 (9)
C10	1.0329 (6)	0.3596 (12)	0.6605 (6)	0.076 (3)*	0.574 (9)
H10A	1.0552	0.4659	0.6273	0.092*	0.574 (9)
H10B	1.0491	0.4138	0.7199	0.092*	0.574 (9)
C11	1.0867 (7)	0.1453 (13)	0.6627 (7)	0.079 (3)*	0.574 (9)
H11A	1.0750	0.0528	0.7052	0.119*	0.574 (9)
H11B	1.1641	0.1661	0.6793	0.119*	0.574 (9)
H11C	1.0556	0.0797	0.6050	0.119*	0.574 (9)
N3A	0.9128 (5)	0.3405 (12)	0.6420 (6)	0.043 (2)*	0.426 (9)
H3A	0.9109	0.2887	0.6901	0.051*	0.426 (9)
C10A	1.0095 (7)	0.2744 (17)	0.6053 (6)	0.065 (3)*	0.426 (9)
H10C	0.9888	0.1537	0.5641	0.078*	0.426 (9)
H10D	1.0334	0.3959	0.5799	0.078*	0.426 (9)
C11A	1.0909 (11)	0.213 (3)	0.6964 (8)	0.111 (5)*	0.426 (9)
H11D	1.0844	0.3111	0.7395	0.167*	0.426 (9)
H11E	1.1639	0.2207	0.6977	0.167*	0.426 (9)
H11F	1.0763	0.0684	0.7100	0.167*	0.426 (9)
H1	0.309 (3)	0.176 (6)	0.535 (2)	0.055 (11)*
H2	0.687 (3)	0.534 (6)	0.556 (2)	0.048 (11)*
H4	0.435 (3)	−0.420 (6)	0.688 (2)	0.050 (10)*
H5	0.634 (3)	−0.414 (6)	0.726 (2)	0.060 (10)*
H8	0.553 (3)	0.336 (5)	0.557 (2)	0.040 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.0450 (6)	0.0550 (6)	0.0933 (8)	−0.0108 (4)	0.0280 (5)	0.0119 (5)
O1	0.0348 (13)	0.0452 (14)	0.0638 (16)	0.0000 (11)	0.0181 (12)	0.0143 (12)
O2	0.0413 (13)	0.0519 (15)	0.0639 (15)	−0.0080 (11)	0.0236 (12)	0.0098 (12)
N1	0.0391 (15)	0.0401 (15)	0.0505 (16)	−0.0012 (12)	0.0217 (13)	0.0044 (13)
N2	0.0349 (15)	0.0393 (16)	0.066 (2)	0.0004 (13)	0.0212 (14)	0.0096 (15)
C1	0.0404 (17)	0.0351 (17)	0.0342 (16)	−0.0023 (13)	0.0181 (14)	−0.0020 (13)
C2	0.0396 (17)	0.0325 (16)	0.0359 (16)	0.0003 (13)	0.0160 (14)	0.0013 (13)
C3	0.0423 (18)	0.0400 (18)	0.0408 (17)	−0.0068 (15)	0.0218 (15)	−0.0035 (15)
C4	0.057 (2)	0.0352 (18)	0.051 (2)	−0.0042 (16)	0.0276 (18)	0.0058 (15)
C5	0.053 (2)	0.0410 (19)	0.051 (2)	0.0068 (16)	0.0245 (17)	0.0094 (16)
C6	0.0388 (17)	0.0431 (18)	0.0468 (19)	0.0040 (15)	0.0197 (15)	0.0012 (15)
C7	0.055 (2)	0.063 (3)	0.075 (3)	−0.0192 (19)	0.035 (2)	0.004 (2)
C8	0.0355 (17)	0.0373 (17)	0.0426 (18)	−0.0004 (15)	0.0151 (14)	0.0042 (15)
C9	0.0367 (18)	0.051 (2)	0.059 (2)	−0.0024 (16)	0.0194 (16)	0.0060 (17)

S1—C9	1.676 (4)	C7—H7C	0.9600
O1—C2	1.360 (4)	C8—H8	0.89 (3)
O1—H1	0.87 (4)	C9—N3A	1.322 (8)
O2—C3	1.367 (4)	C9—N3	1.358 (7)
O2—C7	1.416 (4)	N3—C10	1.661 (8)
N1—C8	1.277 (4)	N3—H3	0.8600
N1—N2	1.376 (4)	C10—C11	1.499 (7)
N2—C9	1.346 (4)	C10—H10A	0.9700
N2—H2	0.82 (3)	C10—H10B	0.9700
C1—C2	1.387 (4)	C11—H11A	0.9600
C1—C6	1.401 (4)	C11—H11B	0.9600
C1—C8	1.454 (4)	C11—H11C	0.9600
C2—C3	1.399 (4)	N3A—C10A	1.667 (8)
C3—C4	1.371 (5)	N3A—H3A	0.8600
C4—C5	1.399 (5)	C10A—C11A	1.506 (7)
C4—H4	0.93 (4)	C10A—H10C	0.9700
C5—C6	1.366 (5)	C10A—H10D	0.9700
C5—H5	1.04 (4)	C11A—H11D	0.9600
C6—H6	0.9300	C11A—H11E	0.9600
C7—H7A	0.9600	C11A—H11F	0.9600
C7—H7B	0.9600
C2—O1—H1	113 (3)	N1—C8—H8	121 (2)
C3—O2—C7	118.0 (3)	C1—C8—H8	118 (2)
C8—N1—N2	115.5 (3)	N3A—C9—N2	116.4 (4)
C9—N2—N1	121.7 (3)	N2—C9—N3	113.1 (4)
C9—N2—H2	120 (2)	N3A—C9—S1	122.0 (4)
N1—N2—H2	118 (2)	N2—C9—S1	120.0 (3)
C2—C1—C6	118.5 (3)	N3—C9—S1	125.5 (3)
C2—C1—C8	119.6 (3)	C9—N3—C10	109.9 (5)
C6—C1—C8	121.9 (3)	C9—N3—H3	125.1
O1—C2—C1	119.0 (3)	C10—N3—H3	125.1
O1—C2—C3	120.3 (3)	C11—C10—N3	101.6 (6)
C1—C2—C3	120.6 (3)	C11—C10—H10A	111.4
O2—C3—C4	126.5 (3)	N3—C10—H10A	111.4
O2—C3—C2	113.5 (3)	C11—C10—H10B	111.4
C4—C3—C2	120.0 (3)	N3—C10—H10B	111.4
C3—C4—C5	119.6 (3)	H10A—C10—H10B	109.3
C3—C4—H4	118 (2)	C9—N3A—C10A	114.2 (6)
C5—C4—H4	122 (2)	C9—N3A—H3A	122.9
C6—C5—C4	120.4 (3)	C10A—N3A—H3A	122.9
C6—C5—H5	116 (2)	C11A—C10A—N3A	93.3 (9)
C4—C5—H5	123 (2)	C11A—C10A—H10C	113.1
C5—C6—C1	120.7 (3)	N3A—C10A—H10C	113.1
C5—C6—H6	119.6	C11A—C10A—H10D	113.1
C1—C6—H6	119.6	N3A—C10A—H10D	113.1
O2—C7—H7A	109.5	H10C—C10A—H10D	110.4
O2—C7—H7B	109.5	C10A—C11A—H11D	109.5
H7A—C7—H7B	109.5	C10A—C11A—H11E	109.5
O2—C7—H7C	109.5	H11D—C11A—H11E	109.5
H7A—C7—H7C	109.5	C10A—C11A—H11F	109.5
H7B—C7—H7C	109.5	H11D—C11A—H11F	109.5
N1—C8—C1	121.5 (3)	H11E—C11A—H11F	109.5
C8—N1—N2—C9	−176.1 (3)	C8—C1—C6—C5	177.8 (3)
C6—C1—C2—O1	179.4 (3)	N2—N1—C8—C1	−177.1 (3)
C8—C1—C2—O1	−0.1 (4)	C2—C1—C8—N1	177.3 (3)
C6—C1—C2—C3	1.5 (4)	C6—C1—C8—N1	−2.2 (5)
C8—C1—C2—C3	−178.0 (3)	N1—N2—C9—N3A	−10.2 (6)
C7—O2—C3—C4	2.6 (5)	N1—N2—C9—N3	16.6 (6)
C7—O2—C3—C2	−177.8 (3)	N1—N2—C9—S1	−176.2 (3)
O1—C2—C3—O2	1.6 (4)	N3A—C9—N3—C10	−54.4 (10)
C1—C2—C3—O2	179.5 (3)	N2—C9—N3—C10	−157.7 (5)
O1—C2—C3—C4	−178.8 (3)	S1—C9—N3—C10	35.9 (8)
C1—C2—C3—C4	−0.9 (5)	C9—N3—C10—C11	−172.4 (6)
O2—C3—C4—C5	−180.0 (3)	N2—C9—N3A—C10A	139.6 (6)
C2—C3—C4—C5	0.5 (5)	N3—C9—N3A—C10A	51.5 (9)
C3—C4—C5—C6	−0.7 (5)	S1—C9—N3A—C10A	−54.8 (9)
C4—C5—C6—C1	1.3 (5)	C9—N3A—C10A—C11A	155.8 (9)
C2—C1—C6—C5	−1.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S1i	0.87 (4)	2.42 (4)	3.169 (3)	145 (3)
N2—H2···O1i	0.82 (3)	2.29 (4)	3.010 (4)	147 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯S1i	0.87 (4)	2.42 (4)	3.169 (3)	145 (3)
N2—H2⋯O1i	0.82 (3)	2.29 (4)	3.010 (4)	147 (3)

Symmetry code: (i) .