4-Methyl-1-(4-methylbenzylidene)thio-semicarbazide.

The title compound, C(10)H(13)N(3)S, prepared by the reaction of 4-methyl-benzaldehyde and 4-methyl-thio-semicarbazide, is approximately planar (r.m.s. deviation for the non-H atoms = 0.032 Å). Its conformation is stabilized by an intra-molecular N-H⋯N hydrogen bond, generating an S(5) ring. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds occur. Further weak N-H⋯S links connect the dimers into (100) sheets.

Related literature

For related structures, see: Li & Jian (2010 ▶); Li et al. (2009 ▶).

Experimental

Crystal data

C10H13N3S

M = 207.29

Monoclinic,

a = 9.1139 (18) Å

b = 13.689 (3) Å

c = 9.1195 (18) Å

β = 91.92 (3)°

V = 1137.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.25 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

10620 measured reflections

2585 independent reflections

1739 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.146

S = 1.14

2585 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.19 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/S1600536810040663/hb5666sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040663/hb5666Isup2.hkl

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

C10H13N3S	F(000) = 440
Mr = 207.29	Dx = 1.211 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1840 reflections
a = 9.1139 (18) Å	θ = 3.3–25.2°
b = 13.689 (3) Å	µ = 0.25 mm−1
c = 9.1195 (18) Å	T = 293 K
β = 91.92 (3)°	Bar, colorless
V = 1137.1 (4) Å3	0.25 × 0.23 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	1739 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 27.5°, θmin = 3.5°
phi and ω scans	h = −11→11
10620 measured reflections	k = −16→17
2585 independent reflections	l = −11→11

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0782P)2 + 0.0376P] where P = (Fo2 + 2Fc2)/3
2585 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.19 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	0.32325 (7)	0.10479 (4)	1.03876 (5)	0.0635 (2)
N3	0.52576 (18)	0.10902 (11)	0.66835 (16)	0.0500 (4)
N2	0.48287 (19)	0.08528 (11)	0.80716 (16)	0.0546 (4)
H2A	0.5276	0.0396	0.8555	0.065*
N1	0.30549 (18)	0.20245 (12)	0.78748 (16)	0.0577 (4)
H1A	0.3375	0.2139	0.7015	0.069*
C2	0.3712 (2)	0.13330 (14)	0.86754 (17)	0.0480 (4)
C4	0.6920 (2)	0.08023 (14)	0.47593 (18)	0.0484 (4)
C7	0.8095 (2)	0.11507 (15)	0.1996 (2)	0.0549 (5)
C3	0.6335 (2)	0.06052 (14)	0.6196 (2)	0.0536 (5)
H3B	0.6757	0.0113	0.6774	0.064*
C9	0.6309 (2)	0.14953 (15)	0.3821 (2)	0.0603 (5)
H9A	0.5496	0.1851	0.4103	0.072*
C5	0.8110 (2)	0.02762 (16)	0.4281 (2)	0.0612 (5)
H5A	0.8527	−0.0204	0.4883	0.073*
C6	0.8688 (2)	0.04527 (18)	0.2926 (2)	0.0656 (6)
H6A	0.9493	0.0093	0.2636	0.079*
C8	0.6893 (3)	0.16642 (16)	0.2469 (2)	0.0640 (6)
H8A	0.6467	0.2137	0.1859	0.077*
C10	0.8716 (3)	0.1343 (2)	0.0510 (2)	0.0766 (7)
H10A	0.9542	0.0921	0.0370	0.115*
H10B	0.9026	0.2012	0.0454	0.115*
H10C	0.7976	0.1217	−0.0240	0.115*
C1	0.1832 (3)	0.2597 (2)	0.8363 (3)	0.0953 (10)
H1B	0.1537	0.3053	0.7611	0.143*
H1C	0.2121	0.2946	0.9239	0.143*
H1D	0.1026	0.2171	0.8564	0.143*

	U11	U22	U33	U12	U13	U23
S1	0.0813 (4)	0.0682 (4)	0.0421 (3)	0.0139 (3)	0.0186 (2)	0.00603 (19)
N3	0.0541 (10)	0.0515 (9)	0.0452 (8)	−0.0020 (7)	0.0137 (7)	0.0010 (6)
N2	0.0613 (11)	0.0587 (9)	0.0444 (8)	0.0068 (8)	0.0135 (7)	0.0048 (6)
N1	0.0608 (11)	0.0644 (10)	0.0491 (8)	0.0117 (8)	0.0193 (7)	0.0127 (7)
C2	0.0525 (11)	0.0490 (10)	0.0430 (9)	−0.0033 (8)	0.0081 (7)	−0.0011 (7)
C4	0.0456 (11)	0.0519 (10)	0.0481 (10)	−0.0013 (8)	0.0075 (7)	−0.0004 (7)
C7	0.0503 (12)	0.0649 (12)	0.0501 (10)	−0.0083 (9)	0.0095 (8)	0.0013 (8)
C3	0.0548 (12)	0.0547 (11)	0.0517 (10)	0.0023 (9)	0.0086 (8)	0.0040 (8)
C9	0.0606 (14)	0.0608 (13)	0.0605 (12)	0.0157 (10)	0.0146 (9)	0.0079 (9)
C5	0.0540 (13)	0.0715 (13)	0.0586 (11)	0.0135 (10)	0.0102 (8)	0.0107 (9)
C6	0.0510 (13)	0.0826 (15)	0.0644 (12)	0.0124 (10)	0.0180 (9)	0.0041 (10)
C8	0.0682 (15)	0.0639 (13)	0.0603 (11)	0.0094 (10)	0.0104 (9)	0.0147 (9)
C10	0.0778 (17)	0.0945 (17)	0.0587 (13)	−0.0095 (14)	0.0226 (11)	0.0069 (11)
C1	0.096 (2)	0.108 (2)	0.0849 (16)	0.0483 (16)	0.0451 (14)	0.0415 (14)

S1—C2	1.6813 (17)	C3—H3B	0.9300
N3—C3	1.277 (2)	C9—C8	1.378 (3)
N3—N2	1.376 (2)	C9—H9A	0.9300
N2—C2	1.345 (2)	C5—C6	1.381 (3)
N2—H2A	0.8600	C5—H5A	0.9300
N1—C2	1.326 (2)	C6—H6A	0.9300
N1—C1	1.444 (3)	C8—H8A	0.9300
N1—H1A	0.8600	C10—H10A	0.9600
C4—C9	1.382 (3)	C10—H10B	0.9600
C4—C5	1.385 (3)	C10—H10C	0.9600
C4—C3	1.456 (2)	C1—H1B	0.9600
C7—C6	1.376 (3)	C1—H1C	0.9600
C7—C8	1.383 (3)	C1—H1D	0.9600
C7—C10	1.509 (2)
C3—N3—N2	116.28 (16)	C6—C5—C4	121.15 (18)
C2—N2—N3	120.22 (16)	C6—C5—H5A	119.4
C2—N2—H2A	119.9	C4—C5—H5A	119.4
N3—N2—H2A	119.9	C7—C6—C5	121.32 (19)
C2—N1—C1	123.79 (16)	C7—C6—H6A	119.3
C2—N1—H1A	118.1	C5—C6—H6A	119.3
C1—N1—H1A	118.1	C9—C8—C7	121.85 (19)
N1—C2—N2	117.22 (15)	C9—C8—H8A	119.1
N1—C2—S1	123.41 (14)	C7—C8—H8A	119.1
N2—C2—S1	119.37 (14)	C7—C10—H10A	109.5
C9—C4—C5	117.71 (17)	C7—C10—H10B	109.5
C9—C4—C3	122.18 (17)	H10A—C10—H10B	109.5
C5—C4—C3	120.09 (17)	C7—C10—H10C	109.5
C6—C7—C8	117.33 (18)	H10A—C10—H10C	109.5
C6—C7—C10	121.6 (2)	H10B—C10—H10C	109.5
C8—C7—C10	121.1 (2)	N1—C1—H1B	109.5
N3—C3—C4	121.71 (18)	N1—C1—H1C	109.5
N3—C3—H3B	119.1	H1B—C1—H1C	109.5
C4—C3—H3B	119.1	N1—C1—H1D	109.5
C8—C9—C4	120.63 (18)	H1B—C1—H1D	109.5
C8—C9—H9A	119.7	H1C—C1—H1D	109.5
C4—C9—H9A	119.7

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.86	2.27	2.644 (2)	107
N1—H1A···S1i	0.86	2.89	3.4869 (16)	128
N2—H2A···S1ii	0.86	2.57	3.4205 (18)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3	0.86	2.27	2.644 (2)	107
N1—H1A⋯S1i	0.86	2.89	3.4869 (16)	128
N2—H2A⋯S1ii	0.86	2.57	3.4205 (18)	171

Symmetry codes: (i) ; (ii) .