Methyl 3-[(E)-1-(4-amino-phen-yl)ethyl-idene]dithio-carbazate.

The title compound, C(10)H(13)N(3)S(2), was obtained from a condensation reaction of methyl dithio-carbazate and 4-amino-acetophenone. In the crystal structure, the nearly planar mol-ecule assumes an E configuration, the benzene ring and dithio-carbazate group being located on opposite sides of the N=C bond. C-H⋯π inter-actions and N-H⋯S hydrogen bonding are present in the crystal structure.

Related literature

For general background, see: Okabe et al. (1993 ▶); Shan et al. (2003 ▶); Jiang (2007 ▶). For related structures, see: Shan et al. (2006 ▶); Zhang et al. (2005 ▶). For synthesis, see: Hu et al. (2001 ▶).

Experimental

Crystal data

C10H13N3S2

M = 239.35

Monoclinic,

a = 10.8247 (12) Å

b = 5.3673 (8) Å

c = 20.4549 (14) Å

β = 94.756 (12)°

V = 1184.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 295 (2) K

0.32 × 0.22 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.870, T max = 0.926

10489 measured reflections

2682 independent reflections

1867 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.124

S = 1.07

2682 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.35 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801283X/om2229sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801283X/om2229Isup2.hkl

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

C10H13N3S2	F000 = 504
Mr = 239.35	Dx = 1.342 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4876 reflections
a = 10.8247 (12) Å	θ = 3.5–25.0º
b = 5.3673 (8) Å	µ = 0.42 mm−1
c = 20.4549 (14) Å	T = 295 (2) K
β = 94.756 (12)º	Prism, yellow
V = 1184.3 (2) Å3	0.32 × 0.22 × 0.20 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2682 independent reflections
Radiation source: fine-focus sealed tube	1867 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
Detector resolution: 10.00 pixels mm-1	θmax = 27.5º
T = 295(2) K	θmin = 3.4º
ω scans	h = −14→14
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	k = −6→6
Tmin = 0.870, Tmax = 0.926	l = −26→26
10489 measured reflections

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0597P)2 + 0.2088P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2682 reflections	Δρmax = 0.32 e Å−3
138 parameters	Δρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.64254 (5)	0.21562 (12)	0.48386 (3)	0.0615 (2)
S2	0.88535 (6)	0.31459 (16)	0.42531 (3)	0.0800 (3)
N1	0.3499 (3)	0.7090 (5)	0.79285 (13)	0.0946 (8)
H1A	0.3635	0.8087	0.8281	0.114*
H1B	0.3062	0.5773	0.8021	0.114*
N2	0.72126 (16)	0.5566 (3)	0.57515 (8)	0.0535 (4)
N3	0.80638 (17)	0.5371 (4)	0.52873 (9)	0.0581 (5)
H3N	0.8845	0.6145	0.5342	0.070*
C1	0.63507 (19)	0.7276 (4)	0.66547 (10)	0.0482 (5)
C2	0.6266 (2)	0.9072 (4)	0.71383 (10)	0.0597 (6)
H2	0.6850	1.0346	0.7178	0.072*
C3	0.5336 (2)	0.9013 (5)	0.75625 (11)	0.0671 (6)
H3	0.5298	1.0257	0.7876	0.081*
C4	0.4458 (2)	0.7123 (5)	0.75263 (11)	0.0630 (6)
C5	0.4553 (2)	0.5303 (5)	0.70511 (13)	0.0691 (6)
H5	0.3980	0.4009	0.7017	0.083*
C6	0.5470 (2)	0.5376 (4)	0.66329 (12)	0.0615 (6)
H6	0.5509	0.4117	0.6323	0.074*
C7	0.73087 (18)	0.7311 (4)	0.61800 (10)	0.0483 (5)
C8	0.8278 (2)	0.9319 (4)	0.62278 (12)	0.0641 (6)
H8A	0.8693	0.9357	0.5831	0.096*
H8B	0.8870	0.8982	0.6593	0.096*
H8C	0.7891	1.0901	0.6290	0.096*
C9	0.78466 (19)	0.3662 (4)	0.48112 (10)	0.0539 (5)
C10	0.6466 (2)	−0.0091 (5)	0.41878 (12)	0.0720 (7)
H10A	0.6459	0.0760	0.3775	0.108*
H10B	0.5753	−0.1157	0.4186	0.108*
H10C	0.7206	−0.1074	0.4255	0.108*

	U11	U22	U33	U12	U13	U23
S1	0.0515 (3)	0.0747 (4)	0.0591 (3)	−0.0119 (3)	0.0090 (2)	−0.0129 (3)
S2	0.0592 (4)	0.1134 (6)	0.0703 (4)	−0.0144 (4)	0.0219 (3)	−0.0215 (4)
N1	0.0967 (18)	0.0956 (18)	0.0979 (17)	0.0018 (14)	0.0456 (14)	−0.0022 (15)
N2	0.0518 (10)	0.0545 (10)	0.0548 (9)	−0.0059 (8)	0.0083 (8)	−0.0056 (9)
N3	0.0511 (10)	0.0621 (11)	0.0621 (10)	−0.0118 (8)	0.0105 (8)	−0.0079 (9)
C1	0.0488 (11)	0.0440 (10)	0.0508 (10)	0.0030 (8)	−0.0019 (8)	−0.0002 (9)
C2	0.0680 (15)	0.0529 (12)	0.0571 (12)	−0.0071 (10)	−0.0020 (10)	−0.0078 (11)
C3	0.0838 (17)	0.0641 (15)	0.0537 (12)	0.0034 (13)	0.0067 (11)	−0.0091 (11)
C4	0.0675 (15)	0.0632 (14)	0.0598 (13)	0.0122 (11)	0.0133 (11)	0.0077 (12)
C5	0.0653 (15)	0.0559 (13)	0.0884 (17)	−0.0078 (11)	0.0197 (12)	−0.0053 (13)
C6	0.0618 (14)	0.0502 (12)	0.0738 (14)	−0.0067 (10)	0.0130 (11)	−0.0143 (11)
C7	0.0469 (11)	0.0439 (10)	0.0526 (11)	0.0002 (8)	−0.0057 (8)	0.0021 (9)
C8	0.0562 (13)	0.0563 (13)	0.0797 (15)	−0.0096 (10)	0.0048 (11)	−0.0079 (12)
C9	0.0477 (11)	0.0618 (13)	0.0525 (11)	−0.0013 (9)	0.0055 (9)	0.0025 (10)
C10	0.0718 (16)	0.0774 (17)	0.0662 (14)	−0.0118 (13)	0.0018 (12)	−0.0185 (13)

S1—C9	1.743 (2)	C2—H2	0.9300
S1—C10	1.800 (2)	C3—C4	1.387 (4)
S2—C9	1.666 (2)	C3—H3	0.9300
N1—C4	1.378 (3)	C4—C5	1.388 (3)
N1—H1A	0.9008	C5—C6	1.364 (3)
N1—H1B	0.8793	C5—H5	0.9300
N2—C7	1.281 (3)	C6—H6	0.9300
N2—N3	1.381 (2)	C7—C8	1.501 (3)
N3—C9	1.345 (3)	C8—H8A	0.9600
N3—H3N	0.9399	C8—H8B	0.9600
C1—C2	1.390 (3)	C8—H8C	0.9600
C1—C6	1.394 (3)	C10—H10A	0.9600
C1—C7	1.478 (3)	C10—H10B	0.9600
C2—C3	1.383 (3)	C10—H10C	0.9600
C9—S1—C10	102.20 (11)	C4—C5—H5	119.4
C4—N1—H1A	112.9	C5—C6—C1	122.2 (2)
C4—N1—H1B	125.7	C5—C6—H6	118.9
H1A—N1—H1B	111.1	C1—C6—H6	118.9
C7—N2—N3	120.32 (17)	N2—C7—C1	114.74 (18)
C9—N3—N2	117.59 (17)	N2—C7—C8	125.9 (2)
C9—N3—H3N	119.2	C1—C7—C8	119.40 (18)
N2—N3—H3N	122.0	C7—C8—H8A	109.5
C2—C1—C6	116.4 (2)	C7—C8—H8B	109.5
C2—C1—C7	123.35 (19)	H8A—C8—H8B	109.5
C6—C1—C7	120.22 (19)	C7—C8—H8C	109.5
C3—C2—C1	121.6 (2)	H8A—C8—H8C	109.5
C3—C2—H2	119.2	H8B—C8—H8C	109.5
C1—C2—H2	119.2	N3—C9—S2	121.66 (16)
C2—C3—C4	121.0 (2)	N3—C9—S1	113.26 (15)
C2—C3—H3	119.5	S2—C9—S1	125.07 (14)
C4—C3—H3	119.5	S1—C10—H10A	109.5
N1—C4—C3	121.6 (2)	S1—C10—H10B	109.5
N1—C4—C5	120.8 (2)	H10A—C10—H10B	109.5
C3—C4—C5	117.5 (2)	S1—C10—H10C	109.5
C6—C5—C4	121.3 (2)	H10A—C10—H10C	109.5
C6—C5—H5	119.4	H10B—C10—H10C	109.5
C7—N2—N3—C9	−173.50 (19)	N3—N2—C7—C1	−178.93 (17)
C6—C1—C2—C3	−1.8 (3)	N3—N2—C7—C8	1.7 (3)
C7—C1—C2—C3	178.2 (2)	C2—C1—C7—N2	−177.2 (2)
C1—C2—C3—C4	1.0 (4)	C6—C1—C7—N2	2.9 (3)
C2—C3—C4—N1	−177.5 (2)	C2—C1—C7—C8	2.3 (3)
C2—C3—C4—C5	0.1 (4)	C6—C1—C7—C8	−177.7 (2)
N1—C4—C5—C6	177.3 (2)	N2—N3—C9—S2	−176.19 (15)
C3—C4—C5—C6	−0.3 (4)	N2—N3—C9—S1	5.0 (2)
C4—C5—C6—C1	−0.6 (4)	C10—S1—C9—N3	−176.49 (17)
C2—C1—C6—C5	1.6 (3)	C10—S1—C9—S2	4.73 (19)
C7—C1—C6—C5	−178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S2i	0.90	2.83	3.722 (3)	170
N3—H3N···S2ii	0.94	2.59	3.483 (2)	159
C10—H10A···Cgiii	0.96	2.80	3.538 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S2i	0.90	2.83	3.722 (3)	170
N3—H3N⋯S2ii	0.94	2.59	3.483 (2)	159
C10—H10A⋯Cgiii	0.96	2.80	3.538 (3)	134

Symmetry codes: (i) ; (ii) ; (iii) . Cg is the centroid of the benzene ring.