(E)-1-(2-Hy-droxy-5-meth-oxy-benzyl-idene)thio-semicarbazide.

In the title mol-ecule, C(9)H(11)N(3)O(2)S, an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked via pairs of N-H⋯S inter-actions, forming inversion dimers with R(2) (2)(8) ring motifs. These dimers are further linked via N-H⋯S and N-H⋯O hydrogen bonds, forming a two-dimensional network lying parallel to (100). The crystal structure is further stabilized by inter-molecular π-π inter-actions [centroid-centroid distance = 3.7972 (9) Å].

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to thio­semicarbazones in coordination chemistry, see: Casas et al. (2000 ▶). For their biological applications, see: Maccioni et al. (2003 ▶); Ferrari et al. (2000 ▶). For related structures, see: Kargar et al. (2010a ▶,b ▶); Adabi Ardakani et al. (2012 ▶).

Experimental

Crystal data

C9H11N3O2S

M = 225.27

Monoclinic,

a = 7.4878 (2) Å

b = 9.9880 (2) Å

c = 14.3754 (3) Å

β = 91.846 (1)°

V = 1074.55 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 291 K

0.24 × 0.14 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.800, T max = 0.926

10176 measured reflections

2673 independent reflections

2365 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.110

S = 1.07

2673 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811056182/su2361sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811056182/su2361Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811056182/su2361Isup3.cml

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

C9H11N3O2S	F(000) = 472
Mr = 225.27	Dx = 1.392 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2750 reflections
a = 7.4878 (2) Å	θ = 2.4–27.5°
b = 9.9880 (2) Å	µ = 0.29 mm−1
c = 14.3754 (3) Å	T = 291 K
β = 91.846 (1)°	Plate, colourless
V = 1074.55 (4) Å3	0.24 × 0.14 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2673 independent reflections
Radiation source: fine-focus sealed tube	2365 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 28.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.800, Tmax = 0.926	k = −13→13
10176 measured reflections	l = −17→19

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0594P)2 + 0.2733P] where P = (Fo2 + 2Fc2)/3
2673 reflections	(Δ/σ)max = 0.001
138 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.26170 (16)	0.48062 (13)	0.97372 (9)	0.0346 (3)
C2	0.24057 (17)	0.58273 (14)	1.03826 (10)	0.0386 (3)
C3	0.2907 (2)	0.71257 (15)	1.01635 (13)	0.0510 (4)
H3	0.2758	0.7812	1.0591	0.061*
C4	0.3626 (2)	0.73967 (16)	0.93147 (14)	0.0573 (4)
H4	0.3962	0.8268	0.9175	0.069*
C5	0.3857 (2)	0.63922 (17)	0.86653 (12)	0.0512 (4)
C6	0.33436 (19)	0.51057 (16)	0.88716 (10)	0.0438 (3)
H6	0.3478	0.4429	0.8435	0.053*
C7	0.4842 (3)	0.5753 (3)	0.71703 (14)	0.0797 (7)
H7A	0.5574	0.5054	0.7437	0.120*
H7B	0.5415	0.6124	0.6641	0.120*
H7C	0.3701	0.5392	0.6978	0.120*
C8	0.21137 (17)	0.34293 (13)	0.99115 (9)	0.0365 (3)
H8	0.2270	0.2798	0.9445	0.044*
C9	0.02639 (18)	0.11834 (12)	1.14708 (9)	0.0353 (3)
N1	0.14624 (14)	0.30443 (10)	1.06812 (8)	0.0349 (2)
N2	0.10299 (16)	0.17032 (11)	1.07211 (8)	0.0388 (3)
H2	0.1255	0.1192	1.0258	0.047*
N3	0.0098 (2)	0.19397 (12)	1.22149 (8)	0.0507 (3)
H3A	0.0478	0.2752	1.2214	0.061*
H3B	−0.0390	0.1620	1.2701	0.061*
O1	0.17090 (17)	0.56061 (11)	1.12351 (8)	0.0514 (3)
H1	0.1484	0.4807	1.1292	0.077*
O2	0.4601 (2)	0.67718 (16)	0.78420 (11)	0.0777 (4)
S1	−0.04238 (6)	−0.04281 (3)	1.14369 (3)	0.04739 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0324 (6)	0.0336 (6)	0.0378 (6)	−0.0011 (5)	0.0011 (5)	0.0040 (5)
C2	0.0356 (6)	0.0346 (6)	0.0455 (7)	0.0003 (5)	0.0019 (5)	0.0011 (5)
C3	0.0486 (8)	0.0323 (7)	0.0722 (10)	−0.0006 (6)	0.0028 (7)	−0.0008 (7)
C4	0.0489 (8)	0.0387 (7)	0.0844 (12)	−0.0041 (6)	0.0022 (8)	0.0213 (8)
C5	0.0422 (7)	0.0543 (9)	0.0573 (9)	−0.0021 (6)	0.0051 (6)	0.0232 (7)
C6	0.0430 (7)	0.0474 (8)	0.0411 (7)	−0.0017 (6)	0.0048 (5)	0.0072 (6)
C7	0.0654 (11)	0.123 (2)	0.0515 (10)	0.0004 (12)	0.0163 (9)	0.0260 (12)
C8	0.0411 (6)	0.0329 (6)	0.0356 (6)	−0.0024 (5)	0.0041 (5)	−0.0009 (5)
C9	0.0440 (6)	0.0293 (6)	0.0326 (6)	0.0004 (5)	0.0021 (5)	0.0016 (5)
N1	0.0401 (5)	0.0285 (5)	0.0362 (5)	−0.0025 (4)	0.0027 (4)	0.0010 (4)
N2	0.0540 (6)	0.0282 (5)	0.0346 (5)	−0.0040 (4)	0.0091 (5)	−0.0012 (4)
N3	0.0834 (9)	0.0347 (6)	0.0347 (6)	−0.0109 (6)	0.0138 (6)	−0.0034 (5)
O1	0.0678 (7)	0.0401 (5)	0.0473 (6)	−0.0046 (5)	0.0163 (5)	−0.0072 (4)
O2	0.0770 (9)	0.0822 (10)	0.0750 (9)	−0.0103 (7)	0.0193 (7)	0.0389 (8)
S1	0.0754 (3)	0.02908 (19)	0.0382 (2)	−0.00904 (14)	0.01049 (17)	0.00096 (12)

C1—C2	1.3912 (19)	C7—H7A	0.9600
C1—C6	1.4063 (18)	C7—H7B	0.9600
C1—C8	1.4499 (17)	C7—H7C	0.9600
C2—O1	1.3653 (17)	C8—N1	1.2824 (16)
C2—C3	1.389 (2)	C8—H8	0.9300
C3—C4	1.376 (2)	C9—N3	1.3187 (17)
C3—H3	0.9300	C9—N2	1.3415 (16)
C4—C5	1.385 (3)	C9—S1	1.6901 (13)
C4—H4	0.9300	N1—N2	1.3797 (14)
C5—C6	1.376 (2)	N2—H2	0.8600
C5—O2	1.3774 (19)	N3—H3A	0.8600
C6—H6	0.9300	N3—H3B	0.8600
C7—O2	1.418 (3)	O1—H1	0.8200
C2—C1—C6	119.32 (13)	H7A—C7—H7B	109.5
C2—C1—C8	122.98 (12)	O2—C7—H7C	109.5
C6—C1—C8	117.70 (12)	H7A—C7—H7C	109.5
O1—C2—C3	117.94 (13)	H7B—C7—H7C	109.5
O1—C2—C1	122.33 (12)	N1—C8—C1	122.80 (12)
C3—C2—C1	119.72 (13)	N1—C8—H8	118.6
C4—C3—C2	120.06 (15)	C1—C8—H8	118.6
C4—C3—H3	120.0	N3—C9—N2	118.93 (12)
C2—C3—H3	120.0	N3—C9—S1	122.17 (10)
C3—C4—C5	121.07 (14)	N2—C9—S1	118.89 (10)
C3—C4—H4	119.5	C8—N1—N2	115.04 (11)
C5—C4—H4	119.5	C9—N2—N1	121.08 (11)
C6—C5—O2	124.45 (17)	C9—N2—H2	119.5
C6—C5—C4	119.29 (14)	N1—N2—H2	119.5
O2—C5—C4	116.26 (15)	C9—N3—H3A	120.0
C5—C6—C1	120.53 (15)	C9—N3—H3B	120.0
C5—C6—H6	119.7	H3A—N3—H3B	120.0
C1—C6—H6	119.7	C2—O1—H1	109.5
O2—C7—H7A	109.5	C5—O2—C7	116.83 (15)
O2—C7—H7B	109.5
C6—C1—C2—O1	179.97 (12)	C2—C1—C6—C5	0.6 (2)
C8—C1—C2—O1	0.2 (2)	C8—C1—C6—C5	−179.64 (13)
C6—C1—C2—C3	0.2 (2)	C2—C1—C8—N1	−1.2 (2)
C8—C1—C2—C3	−179.54 (13)	C6—C1—C8—N1	179.03 (12)
O1—C2—C3—C4	179.62 (14)	C1—C8—N1—N2	178.93 (11)
C1—C2—C3—C4	−0.6 (2)	N3—C9—N2—N1	−7.2 (2)
C2—C3—C4—C5	0.2 (2)	S1—C9—N2—N1	173.92 (10)
C3—C4—C5—C6	0.6 (2)	C8—N1—N2—C9	−177.01 (12)
C3—C4—C5—O2	−179.49 (14)	C6—C5—O2—C7	0.0 (2)
O2—C5—C6—C1	179.10 (14)	C4—C5—O2—C7	−179.90 (16)
C4—C5—C6—C1	−1.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.97	2.6844 (15)	146
N2—H2···S1i	0.86	2.61	3.3706 (12)	148
N3—H3A···S1ii	0.86	2.66	3.2706 (12)	129
N3—H3B···O1iii	0.86	2.11	2.9604 (17)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.97	2.6844 (15)	146
N2—H2⋯S1i	0.86	2.61	3.3706 (12)	148
N3—H3A⋯S1ii	0.86	2.66	3.2706 (12)	129
N3—H3B⋯O1iii	0.86	2.11	2.9604 (17)	172

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