1-(4-Meth-oxy-benzyl-idene)-4-methyl-thiosemicarbazide.

The title compound, C(10)H(13)N(3)OS, was prepared by the reaction of 4-meth-oxy-benzaldehyde and 4-methyl-thio-semicarbazide. The dihedral angle between the benzene ring and the thio-urea unit is 8.64 (7)° and an intra-molecular N-H⋯N hydrogen bond generates an S(5) ring. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate R(2) (2)(8) loops. The dimers are linked into (001) sheets by further N-H⋯S links.

Related literature

For background to Schiff bases, see: Casas et al. (2000 ▶). For a related structure, see: Li & Jian (2010 ▶).

Experimental

Crystal data

C10H13N3OS

M = 223.29

Orthorhombic,

a = 13.397 (3) Å

b = 9.1271 (18) Å

c = 18.799 (4) Å

V = 2298.6 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.25 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

20742 measured reflections

2627 independent reflections

1746 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.146

S = 0.94

2627 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038882/hb5659sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038882/hb5659Isup2.hkl

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

C10H13N3OS	Dx = 1.290 Mg m−3
Mr = 223.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2650 reflections
a = 13.397 (3) Å	θ = 3.2–27.2°
b = 9.1271 (18) Å	µ = 0.26 mm−1
c = 18.799 (4) Å	T = 293 K
V = 2298.6 (8) Å3	Bar, colorless
Z = 8	0.25 × 0.22 × 0.18 mm
F(000) = 944

Bruker SMART CCD area-detector diffractometer	1746 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
graphite	θmax = 27.5°, θmin = 3.0°
phi and ω scans	h = −17→17
20742 measured reflections	k = −11→11
2627 independent reflections	l = −24→24

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2627 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.29 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
S1	0.89733 (4)	1.04305 (5)	0.58910 (3)	0.0579 (2)
C7	0.89674 (13)	0.2105 (2)	0.33447 (9)	0.0442 (4)
N3	0.88845 (12)	0.66880 (17)	0.48831 (8)	0.0467 (4)
C4	0.92228 (14)	0.4806 (2)	0.40190 (10)	0.0456 (4)
O1	0.88816 (11)	0.08431 (16)	0.29666 (7)	0.0577 (4)
N2	0.91161 (12)	0.80887 (17)	0.50939 (9)	0.0509 (4)
H2A	0.9558	0.8577	0.4862	0.061*
C8	0.85569 (15)	0.2343 (2)	0.40146 (9)	0.0483 (5)
H8A	0.8197	0.1606	0.4240	0.058*
C2	0.86618 (14)	0.8710 (2)	0.56577 (10)	0.0450 (4)
N1	0.79800 (13)	0.79216 (17)	0.59919 (8)	0.0567 (5)
H1A	0.7848	0.7061	0.5831	0.068*
C9	0.86880 (15)	0.3681 (2)	0.43415 (10)	0.0484 (5)
H9A	0.8412	0.3836	0.4789	0.058*
C3	0.93581 (15)	0.6236 (2)	0.43363 (10)	0.0505 (5)
H3B	0.9819	0.6866	0.4129	0.061*
C5	0.96339 (16)	0.4532 (2)	0.33528 (10)	0.0550 (5)
H5A	1.0006	0.5259	0.3130	0.066*
C10	0.83329 (19)	−0.0329 (2)	0.32630 (13)	0.0661 (6)
H10A	0.8337	−0.1143	0.2940	0.099*
H10B	0.7657	−0.0023	0.3345	0.099*
H10C	0.8631	−0.0619	0.3706	0.099*
C6	0.95017 (17)	0.3214 (2)	0.30188 (10)	0.0584 (5)
H6A	0.9773	0.3063	0.2569	0.070*
C1	0.7442 (2)	0.8428 (3)	0.66153 (12)	0.0832 (8)
H1B	0.6985	0.7681	0.6769	0.125*
H1C	0.7077	0.9301	0.6499	0.125*
H1D	0.7907	0.8636	0.6990	0.125*

	U11	U22	U33	U12	U13	U23
S1	0.0564 (4)	0.0466 (3)	0.0707 (4)	−0.0056 (2)	0.0113 (2)	−0.0107 (2)
C7	0.0415 (9)	0.0505 (10)	0.0405 (9)	−0.0008 (7)	0.0004 (7)	−0.0047 (8)
N3	0.0450 (9)	0.0478 (9)	0.0473 (8)	−0.0012 (7)	0.0014 (7)	−0.0062 (7)
C4	0.0398 (10)	0.0524 (10)	0.0446 (10)	−0.0010 (8)	0.0011 (8)	−0.0025 (8)
O1	0.0616 (9)	0.0578 (8)	0.0537 (8)	−0.0079 (6)	0.0076 (6)	−0.0105 (7)
N2	0.0492 (10)	0.0480 (9)	0.0557 (9)	−0.0070 (7)	0.0083 (7)	−0.0079 (7)
C8	0.0510 (11)	0.0498 (10)	0.0441 (10)	−0.0016 (9)	0.0055 (8)	0.0060 (8)
C2	0.0393 (9)	0.0470 (10)	0.0488 (10)	0.0024 (8)	−0.0009 (8)	−0.0009 (8)
N1	0.0623 (11)	0.0511 (9)	0.0568 (10)	−0.0110 (8)	0.0156 (8)	−0.0102 (8)
C9	0.0512 (11)	0.0553 (11)	0.0386 (9)	0.0006 (9)	0.0067 (8)	0.0011 (8)
C3	0.0456 (11)	0.0534 (11)	0.0524 (11)	−0.0051 (9)	0.0023 (9)	−0.0020 (9)
C5	0.0572 (12)	0.0587 (12)	0.0492 (10)	−0.0129 (9)	0.0156 (9)	−0.0027 (9)
C10	0.0698 (16)	0.0533 (12)	0.0751 (14)	−0.0098 (10)	0.0038 (12)	−0.0050 (10)
C6	0.0602 (13)	0.0689 (13)	0.0462 (10)	−0.0105 (10)	0.0168 (9)	−0.0102 (9)
C1	0.099 (2)	0.0764 (14)	0.0739 (14)	−0.0251 (14)	0.0394 (15)	−0.0209 (13)

S1—C2	1.683 (2)	C2—N1	1.322 (2)
C7—O1	1.358 (2)	N1—C1	1.451 (3)
C7—C6	1.383 (3)	N1—H1A	0.8600
C7—C8	1.391 (3)	C9—H9A	0.9300
N3—C3	1.277 (2)	C3—H3B	0.9300
N3—N2	1.374 (2)	C5—C6	1.368 (3)
C4—C5	1.391 (3)	C5—H5A	0.9300
C4—C9	1.391 (3)	C10—H10A	0.9600
C4—C3	1.446 (3)	C10—H10B	0.9600
O1—C10	1.413 (2)	C10—H10C	0.9600
N2—C2	1.347 (2)	C6—H6A	0.9300
N2—H2A	0.8600	C1—H1B	0.9600
C8—C9	1.378 (3)	C1—H1C	0.9600
C8—H8A	0.9300	C1—H1D	0.9600
O1—C7—C6	115.63 (16)	C4—C9—H9A	119.2
O1—C7—C8	124.96 (17)	N3—C3—C4	124.16 (18)
C6—C7—C8	119.40 (17)	N3—C3—H3B	117.9
C3—N3—N2	114.88 (16)	C4—C3—H3B	117.9
C5—C4—C9	117.63 (17)	C6—C5—C4	121.34 (17)
C5—C4—C3	118.95 (17)	C6—C5—H5A	119.3
C9—C4—C3	123.42 (17)	C4—C5—H5A	119.3
C7—O1—C10	118.68 (15)	O1—C10—H10A	109.5
C2—N2—N3	121.08 (16)	O1—C10—H10B	109.5
C2—N2—H2A	119.5	H10A—C10—H10B	109.5
N3—N2—H2A	119.5	O1—C10—H10C	109.5
C9—C8—C7	119.47 (18)	H10A—C10—H10C	109.5
C9—C8—H8A	120.3	H10B—C10—H10C	109.5
C7—C8—H8A	120.3	C5—C6—C7	120.48 (17)
N1—C2—N2	117.22 (17)	C5—C6—H6A	119.8
N1—C2—S1	123.74 (15)	C7—C6—H6A	119.8
N2—C2—S1	119.04 (15)	N1—C1—H1B	109.5
C2—N1—C1	123.65 (17)	N1—C1—H1C	109.5
C2—N1—H1A	118.2	H1B—C1—H1C	109.5
C1—N1—H1A	118.2	N1—C1—H1D	109.5
C8—C9—C4	121.67 (17)	H1B—C1—H1D	109.5
C8—C9—H9A	119.2	H1C—C1—H1D	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.86	2.28	2.661 (2)	107
N1—H1A···S1i	0.86	2.86	3.4718 (18)	130
N2—H2A···S1ii	0.86	2.59	3.4359 (17)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3	0.86	2.28	2.661 (2)	107
N1—H1A⋯S1i	0.86	2.86	3.4718 (18)	130
N2—H2A⋯S1ii	0.86	2.59	3.4359 (17)	169

Symmetry codes: (i) ; (ii) .