(E)-1-[4-(Dimethyl-amino)benzyl-idene]thio-semicarbazide.

In the title mol-ecule, C(10)H(14)N(4)S, the thio-rea plane and benzene ring form a dihedral angle of 16.0 (3) Å. In the crystal structure, inter-molecular N-H⋯S hydrogen bonds link the mol-ecules into ribbons extended in the [100] direction; these incorporate inversion dimers.

Related literature

For the biomedical properties of thio­semicarbazones, see: Beraldo & Gambino (2004 ▶); Bondock et al. (2007 ▶). For the crystal structure of the related compound benzyl N′-(2-chloro­benzyl­idene)hydrazinecarbodithio­ate, see Shi et al. (2008 ▶).

Experimental

Crystal data

C10H14N4S

M = 222.31

Monoclinic,

a = 5.6984 (13) Å

b = 8.9493 (14) Å

c = 22.813 (2) Å

β = 93.860 (2)°

V = 1160.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 298 (2) K

0.50 × 0.48 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.884, T max = 0.937

5769 measured reflections

2047 independent reflections

1435 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 1.02

2047 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 I, global. DOI: 10.1107/S1600536808043778/cv2492sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043778/cv2492Isup2.hkl

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

C10H14N4S	F(000) = 472
Mr = 222.31	Dx = 1.272 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.6984 (13) Å	Cell parameters from 2093 reflections
b = 8.9493 (14) Å	θ = 2.5–25.9°
c = 22.813 (2) Å	µ = 0.25 mm−1
β = 93.860 (2)°	T = 298 K
V = 1160.7 (3) Å3	Block, orange
Z = 4	0.50 × 0.48 × 0.26 mm

Bruker SMART CCD area-detector diffractometer	2047 independent reflections
Radiation source: fine-focus sealed tube	1435 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.884, Tmax = 0.937	k = −10→10
5769 measured reflections	l = −27→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.4004P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2047 reflections	Δρmax = 0.17 e Å−3
137 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (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
N1	0.9364 (3)	0.1808 (2)	0.14592 (8)	0.0544 (5)
H1	1.0442	0.2390	0.1611	0.065*
N2	0.7454 (3)	0.1467 (2)	0.17756 (8)	0.0497 (5)
N3	0.7772 (3)	0.0474 (2)	0.06910 (8)	0.0583 (6)
H3A	0.6548	0.0349	0.0887	0.070*
H3B	0.7820	0.0093	0.0346	0.070*
N4	0.0633 (3)	0.1090 (2)	0.39241 (9)	0.0621 (6)
S1	1.20240 (11)	0.15551 (9)	0.05735 (3)	0.0708 (3)
C1	0.9570 (4)	0.1249 (2)	0.09195 (9)	0.0473 (5)
C2	0.7371 (4)	0.2136 (3)	0.22678 (9)	0.0510 (6)
H2	0.8539	0.2829	0.2374	0.061*
C3	0.5554 (4)	0.1872 (2)	0.26677 (9)	0.0470 (5)
C4	0.5549 (4)	0.2699 (3)	0.31838 (10)	0.0560 (6)
H4	0.6676	0.3441	0.3253	0.067*
C5	0.3937 (4)	0.2457 (3)	0.35945 (10)	0.0573 (6)
H5	0.3985	0.3044	0.3932	0.069*
C6	0.2228 (4)	0.1346 (2)	0.35143 (9)	0.0483 (5)
C7	0.2210 (4)	0.0514 (3)	0.29886 (9)	0.0528 (6)
H7	0.1082	−0.0226	0.2916	0.063*
C8	0.3831 (4)	0.0782 (3)	0.25809 (9)	0.0507 (6)
H8	0.3771	0.0217	0.2238	0.061*
C9	−0.1011 (4)	−0.0139 (3)	0.38610 (12)	0.0684 (7)
H9A	−0.1877	−0.0074	0.3486	0.103*
H9B	−0.2082	−0.0092	0.4168	0.103*
H9C	−0.0166	−0.1067	0.3887	0.103*
C10	0.0832 (6)	0.1853 (3)	0.44832 (12)	0.0900 (10)
H10A	0.2193	0.1495	0.4711	0.135*
H10B	−0.0549	0.1664	0.4690	0.135*
H10C	0.0984	0.2908	0.4419	0.135*

	U11	U22	U33	U12	U13	U23
N1	0.0517 (11)	0.0650 (13)	0.0474 (11)	−0.0059 (9)	0.0093 (9)	−0.0067 (10)
N2	0.0506 (10)	0.0566 (12)	0.0425 (10)	0.0063 (9)	0.0089 (8)	0.0035 (9)
N3	0.0458 (10)	0.0862 (15)	0.0438 (11)	−0.0059 (10)	0.0098 (8)	−0.0078 (10)
N4	0.0661 (12)	0.0674 (14)	0.0547 (12)	−0.0014 (10)	0.0186 (10)	−0.0096 (10)
S1	0.0521 (4)	0.0967 (6)	0.0658 (5)	−0.0157 (3)	0.0204 (3)	−0.0145 (4)
C1	0.0442 (12)	0.0545 (14)	0.0433 (12)	0.0065 (10)	0.0034 (9)	0.0047 (10)
C2	0.0608 (13)	0.0469 (13)	0.0454 (13)	0.0028 (11)	0.0048 (11)	0.0003 (10)
C3	0.0582 (13)	0.0433 (13)	0.0396 (12)	0.0080 (10)	0.0041 (10)	0.0000 (10)
C4	0.0701 (15)	0.0447 (13)	0.0541 (14)	−0.0055 (11)	0.0105 (12)	−0.0073 (11)
C5	0.0776 (16)	0.0499 (14)	0.0455 (13)	0.0010 (12)	0.0125 (12)	−0.0134 (11)
C6	0.0521 (12)	0.0480 (13)	0.0450 (13)	0.0087 (10)	0.0042 (10)	−0.0018 (10)
C7	0.0521 (12)	0.0561 (15)	0.0499 (13)	−0.0030 (11)	0.0018 (10)	−0.0084 (11)
C8	0.0583 (13)	0.0545 (14)	0.0389 (12)	0.0055 (11)	−0.0010 (10)	−0.0095 (10)
C9	0.0647 (15)	0.0705 (17)	0.0714 (17)	−0.0004 (13)	0.0154 (13)	0.0057 (14)
C10	0.118 (2)	0.088 (2)	0.0690 (19)	−0.0113 (18)	0.0441 (17)	−0.0195 (16)

N1—C1	1.342 (3)	C4—C5	1.372 (3)
N1—N2	1.380 (2)	C4—H4	0.9300
N1—H1	0.8600	C5—C6	1.396 (3)
N2—C2	1.276 (3)	C5—H5	0.9300
N3—C1	1.315 (3)	C6—C7	1.411 (3)
N3—H3A	0.8600	C7—C8	1.375 (3)
N3—H3B	0.8600	C7—H7	0.9300
N4—C6	1.366 (3)	C8—H8	0.9300
N4—C10	1.445 (3)	C9—H9A	0.9600
N4—C9	1.446 (3)	C9—H9B	0.9600
S1—C1	1.674 (2)	C9—H9C	0.9600
C2—C3	1.445 (3)	C10—H10A	0.9600
C2—H2	0.9300	C10—H10B	0.9600
C3—C8	1.389 (3)	C10—H10C	0.9600
C3—C4	1.391 (3)
C1—N1—N2	121.22 (18)	C4—C5—H5	119.5
C1—N1—H1	119.4	C6—C5—H5	119.5
N2—N1—H1	119.4	N4—C6—C5	121.3 (2)
C2—N2—N1	115.69 (19)	N4—C6—C7	121.8 (2)
C1—N3—H3A	120.0	C5—C6—C7	116.9 (2)
C1—N3—H3B	120.0	C8—C7—C6	121.1 (2)
H3A—N3—H3B	120.0	C8—C7—H7	119.5
C6—N4—C10	120.6 (2)	C6—C7—H7	119.5
C6—N4—C9	121.0 (2)	C7—C8—C3	121.8 (2)
C10—N4—C9	117.4 (2)	C7—C8—H8	119.1
N3—C1—N1	116.51 (19)	C3—C8—H8	119.1
N3—C1—S1	123.55 (17)	N4—C9—H9A	109.5
N1—C1—S1	119.94 (17)	N4—C9—H9B	109.5
N2—C2—C3	123.3 (2)	H9A—C9—H9B	109.5
N2—C2—H2	118.3	N4—C9—H9C	109.5
C3—C2—H2	118.3	H9A—C9—H9C	109.5
C8—C3—C4	116.9 (2)	H9B—C9—H9C	109.5
C8—C3—C2	123.7 (2)	N4—C10—H10A	109.5
C4—C3—C2	119.3 (2)	N4—C10—H10B	109.5
C5—C4—C3	122.3 (2)	H10A—C10—H10B	109.5
C5—C4—H4	118.9	N4—C10—H10C	109.5
C3—C4—H4	118.9	H10A—C10—H10C	109.5
C4—C5—C6	121.1 (2)	H10B—C10—H10C	109.5
C1—N1—N2—C2	−175.76 (19)	C9—N4—C6—C5	−175.0 (2)
N2—N1—C1—N3	5.8 (3)	C10—N4—C6—C7	173.9 (2)
N2—N1—C1—S1	−174.31 (15)	C9—N4—C6—C7	5.8 (3)
N1—N2—C2—C3	−177.43 (18)	C4—C5—C6—N4	179.4 (2)
N2—C2—C3—C8	5.5 (3)	C4—C5—C6—C7	−1.4 (3)
N2—C2—C3—C4	−177.3 (2)	N4—C6—C7—C8	−179.8 (2)
C8—C3—C4—C5	0.4 (3)	C5—C6—C7—C8	0.9 (3)
C2—C3—C4—C5	−177.0 (2)	C6—C7—C8—C3	0.2 (3)
C3—C4—C5—C6	0.7 (4)	C4—C3—C8—C7	−0.8 (3)
C10—N4—C6—C5	−6.9 (4)	C2—C3—C8—C7	176.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···S1i	0.86	2.84	3.408 (2)	125
N3—H3B···S1ii	0.86	2.57	3.417 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯S1i	0.86	2.84	3.408 (2)	125
N3—H3B⋯S1ii	0.86	2.57	3.417 (2)	168

Symmetry codes: (i) ; (ii) .