Crystal structure of S-hexyl (E)-3-(4-methyl-benzyl-idene)di-thio-carbazate.

In the title compound, C15H22N2S2, the di-thio-carbazate group adopts an E conformation with respect to the C=N bond of the benzyl-idene moiety. In the crystal, mol-ecules are linked by pairs of N-H⋯S hydrogen bonds, forming inversion dimers with an R (2) 2(8) ring motif. The dimers are linked via C-H⋯π inter-actions, forming chains propagating along [100].

Related literature

For the biological properties of bidentate Schiff bases of S-methyl di­thio­carbazate or S-benzyl di­thio­carbaza­te and their bivalent n class="Chemical">metal complexes, see: Chan et al. (2008 ▸); How et al. (2008 ▸); Tarafder et al. (2002 ▸); Ali et al. (2002 ▸); Chew et al. (2004 ▸); Crouse et al. (2004 ▸). For their N,S-chelating behavior towards metal atoms, see for example: Islam et al. (2011 ▸). For the structures of related compounds, see: Tarafder et al. (2008 ▸, 2010 ▸).

Experimental

Crystal data

C15H22N2S2

M = 294.47

Triclinic,

a = 4.79244 (9) Å

b = 11.3790 (2) Å

c = 14.5382 (3) Å

α = 100.1666 (7)°

β = 91.2117 (7)°

γ = 94.6754 (7)°

V = 777.26 (3) Å3

Z = 2

Cu Kα radiation

μ = 3.00 mm−1

T = 173 K

0.19 × 0.11 × 0.07 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Rigaku, 2001 ▸) T min = 0.615, T max = 0.811

8970 measured reflections

2802 independent reflections

2162 reflections with F 2 > 2.0σ(F 2)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.129

S = 1.04

2802 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.26 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2001 ▸); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: CrystalStructure (Rigaku, 2010 ▸); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S2056989015000080/su5050sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015000080/su5050Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015000080/su5050Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015000080/su5050fig1.tif

A view of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015000080/su5050fig2.tif

A partial view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity).

CCDC reference: 1035819

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H22N2S2	Z = 2
Mr = 294.47	F(000) = 316.00
Triclinic, P1	Dx = 1.258 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54187 Å
a = 4.79244 (9) Å	Cell parameters from 7029 reflections
b = 11.3790 (2) Å	θ = 3.1–68.2°
c = 14.5382 (3) Å	µ = 3.00 mm−1
α = 100.1666 (7)°	T = 173 K
β = 91.2117 (7)°	Prism, colorless
γ = 94.6754 (7)°	0.19 × 0.11 × 0.07 mm
V = 777.26 (3) Å3

Rigaku R-AXIS RAPID diffractometer	2162 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.000 pixels mm-1	Rint = 0.052
ω scans	θmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Rigaku, 2001)	h = −5→5
Tmin = 0.615, Tmax = 0.811	k = −13→13
8970 measured reflections	l = −17→17
2802 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0784P)2] where P = (Fo2 + 2Fc2)/3
2802 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.26 e Å−3
Primary atom site location: structure-invariant direct methods

Experimental. 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.

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
S1	1.54116 (12)	0.83289 (5)	0.90597 (4)	0.0326 (2)
S2	1.17201 (12)	0.64667 (5)	0.98677 (4)	0.0333 (2)
N1	1.0048 (4)	0.84542 (15)	1.10436 (12)	0.0293 (5)
N2	1.2012 (4)	0.87708 (16)	1.04349 (13)	0.0297 (5)
C1	0.0848 (5)	0.8428 (3)	1.42942 (17)	0.0390 (6)
C2	0.2994 (5)	0.8663 (2)	1.35925 (15)	0.0300 (5)
C3	0.3922 (5)	0.77235 (19)	1.29544 (15)	0.0333 (6)
C4	0.5864 (5)	0.79268 (19)	1.23002 (15)	0.0327 (6)
C5	0.6987 (5)	0.90853 (18)	1.22664 (14)	0.0282 (5)
C6	0.6060 (5)	1.00311 (19)	1.28972 (15)	0.0314 (6)
C7	0.4103 (5)	0.9817 (2)	1.35483 (15)	0.0334 (6)
C8	0.9098 (5)	0.93191 (19)	1.15966 (15)	0.0281 (5)
C9	1.3050 (5)	0.79357 (19)	0.98029 (15)	0.0290 (5)
C10	1.3277 (5)	0.55512 (19)	0.88956 (15)	0.0329 (6)
C11	1.1314 (5)	0.51925 (18)	0.80356 (15)	0.0333 (6)
C12	1.0591 (5)	0.62287 (19)	0.75707 (15)	0.0329 (6)
C13	0.8582 (5)	0.58746 (19)	0.67205 (15)	0.0330 (6)
C14	0.7870 (5)	0.69523 (19)	0.63000 (16)	0.0363 (6)
C15	0.5920 (6)	0.6635 (3)	0.54445 (17)	0.0445 (7)
H1	0.0707	0.7576	1.4338	0.0468*
H2	−0.0975	0.8647	1.4095	0.0468*
H3	0.1417	0.8908	1.4907	0.0468*
H4	0.3201	0.6925	1.2971	0.0400*
H5	0.6440	0.7270	1.1869	0.0393*
H6	0.6778	1.0830	1.2880	0.0377*
H7	0.3505	1.0474	1.3974	0.0401*
H8	0.9772	1.0121	1.1572	0.0337*
H9	1.266 (5)	0.948 (3)	1.0471 (17)	0.044 (8)*
H10	1.4987	0.6000	0.8723	0.0395*
H11	1.3848	0.4817	0.9098	0.0395*
H12	1.2193	0.4603	0.7573	0.0400*
H13	0.9556	0.4791	0.8220	0.0400*
H14	1.2346	0.6621	0.7376	0.0394*
H15	0.9745	0.6826	0.8037	0.0394*
H16	0.9442	0.5300	0.6240	0.0396*
H17	0.6834	0.5467	0.6907	0.0396*
H18	0.6990	0.7519	0.6781	0.0435*
H19	0.9628	0.7367	0.6129	0.0435*
H20	0.5574	0.7366	0.5206	0.0534*
H21	0.4142	0.6253	0.5612	0.0534*
H22	0.6782	0.6081	0.4961	0.0534*

	U11	U22	U33	U12	U13	U23
S1	0.0382 (4)	0.0272 (4)	0.0329 (4)	0.0014 (3)	0.0096 (3)	0.0062 (3)
S2	0.0453 (5)	0.0245 (3)	0.0317 (4)	0.0021 (3)	0.0077 (3)	0.0087 (3)
N1	0.0353 (12)	0.0273 (10)	0.0259 (10)	0.0011 (9)	0.0034 (9)	0.0070 (8)
N2	0.0342 (12)	0.0236 (10)	0.0318 (11)	0.0010 (9)	0.0072 (9)	0.0062 (8)
C1	0.0374 (15)	0.0452 (14)	0.0383 (14)	0.0048 (12)	0.0056 (11)	0.0169 (11)
C2	0.0308 (14)	0.0345 (12)	0.0266 (12)	0.0037 (10)	−0.0019 (10)	0.0104 (10)
C3	0.0404 (15)	0.0240 (11)	0.0361 (13)	−0.0023 (10)	0.0017 (11)	0.0091 (10)
C4	0.0413 (15)	0.0255 (11)	0.0312 (12)	0.0045 (11)	0.0007 (11)	0.0039 (10)
C5	0.0324 (14)	0.0268 (11)	0.0263 (12)	0.0034 (10)	−0.0014 (10)	0.0071 (9)
C6	0.0350 (14)	0.0238 (11)	0.0364 (13)	0.0016 (10)	0.0032 (11)	0.0079 (10)
C7	0.0399 (15)	0.0290 (12)	0.0314 (12)	0.0060 (11)	0.0044 (11)	0.0033 (10)
C8	0.0296 (13)	0.0255 (11)	0.0304 (12)	0.0025 (10)	0.0003 (10)	0.0083 (9)
C9	0.0333 (14)	0.0280 (11)	0.0274 (11)	0.0054 (10)	−0.0011 (10)	0.0084 (9)
C10	0.0406 (15)	0.0249 (11)	0.0346 (13)	0.0086 (11)	0.0042 (11)	0.0061 (10)
C11	0.0416 (15)	0.0245 (11)	0.0350 (13)	0.0034 (11)	0.0046 (11)	0.0074 (10)
C12	0.0396 (15)	0.0254 (11)	0.0345 (13)	0.0044 (10)	0.0050 (11)	0.0069 (10)
C13	0.0362 (14)	0.0272 (12)	0.0364 (13)	0.0021 (10)	0.0056 (11)	0.0077 (10)
C14	0.0416 (16)	0.0301 (12)	0.0388 (13)	0.0035 (11)	0.0048 (12)	0.0100 (10)
C15	0.0494 (17)	0.0415 (14)	0.0449 (15)	0.0004 (13)	−0.0021 (13)	0.0160 (12)

S1—C9	1.670 (3)	C1—H2	0.980
S2—C9	1.759 (3)	C1—H3	0.980
S2—C10	1.814 (3)	C3—H4	0.950
N1—N2	1.375 (3)	C4—H5	0.950
N1—C8	1.277 (3)	C6—H6	0.950
N2—C9	1.335 (3)	C7—H7	0.950
C1—C2	1.505 (4)	C8—H8	0.950
C2—C3	1.395 (3)	C10—H10	0.990
C2—C7	1.389 (4)	C10—H11	0.990
C3—C4	1.380 (4)	C11—H12	0.990
C4—C5	1.392 (3)	C11—H13	0.990
C5—C6	1.394 (3)	C12—H14	0.990
C5—C8	1.460 (4)	C12—H15	0.990
C6—C7	1.384 (4)	C13—H16	0.990
C10—C11	1.524 (3)	C13—H17	0.990
C11—C12	1.518 (4)	C14—H18	0.990
C12—C13	1.526 (3)	C14—H19	0.990
C13—C14	1.523 (4)	C15—H20	0.980
C14—C15	1.512 (4)	C15—H21	0.980
N2—H9	0.84 (3)	C15—H22	0.980
C1—H1	0.980
C9—S2—C10	103.78 (11)	C2—C7—H7	119.297
N2—N1—C8	115.97 (18)	C6—C7—H7	119.294
N1—N2—C9	120.61 (18)	N1—C8—H8	119.724
C1—C2—C3	120.9 (2)	C5—C8—H8	119.729
C1—C2—C7	121.6 (2)	S2—C10—H10	108.909
C3—C2—C7	117.5 (2)	S2—C10—H11	108.910
C2—C3—C4	121.5 (2)	C11—C10—H10	108.900
C3—C4—C5	120.6 (2)	C11—C10—H11	108.913
C4—C5—C6	118.3 (2)	H10—C10—H11	107.737
C4—C5—C8	121.55 (19)	C10—C11—H12	108.647
C6—C5—C8	120.14 (19)	C10—C11—H13	108.645
C5—C6—C7	120.6 (2)	C12—C11—H12	108.656
C2—C7—C6	121.4 (2)	C12—C11—H13	108.654
N1—C8—C5	120.5 (2)	H12—C11—H13	107.587
S1—C9—S2	126.25 (13)	C11—C12—H14	108.631
S1—C9—N2	120.30 (17)	C11—C12—H15	108.636
S2—C9—N2	113.44 (17)	C13—C12—H14	108.637
S2—C10—C11	113.33 (17)	C13—C12—H15	108.627
C10—C11—C12	114.44 (17)	H14—C12—H15	107.578
C11—C12—C13	114.52 (18)	C12—C13—H16	109.166
C12—C13—C14	112.20 (17)	C12—C13—H17	109.171
C13—C14—C15	113.80 (18)	C14—C13—H16	109.159
N1—N2—H9	121.2 (17)	C14—C13—H17	109.167
C9—N2—H9	118.1 (17)	H16—C13—H17	107.879
C2—C1—H1	109.474	C13—C14—H18	108.795
C2—C1—H2	109.467	C13—C14—H19	108.797
C2—C1—H3	109.465	C15—C14—H18	108.803
H1—C1—H2	109.474	C15—C14—H19	108.808
H1—C1—H3	109.480	H18—C14—H19	107.672
H2—C1—H3	109.467	C14—C15—H20	109.472
C2—C3—H4	119.227	C14—C15—H21	109.469
C4—C3—H4	119.232	C14—C15—H22	109.470
C3—C4—H5	119.709	H20—C15—H21	109.471
C5—C4—H5	119.710	H20—C15—H22	109.473
C5—C6—H6	119.686	H21—C15—H22	109.472
C7—C6—H6	119.692
C9—S2—C10—C11	−99.27 (15)	C3—C4—C5—C6	−1.2 (4)
C10—S2—C9—S1	−4.68 (19)	C3—C4—C5—C8	178.37 (19)
C10—S2—C9—N2	176.19 (15)	C4—C5—C6—C7	0.9 (4)
N2—N1—C8—C5	179.48 (17)	C4—C5—C8—N1	−2.6 (4)
C8—N1—N2—C9	−177.29 (18)	C6—C5—C8—N1	176.96 (19)
N1—N2—C9—S1	179.41 (16)	C8—C5—C6—C7	−178.62 (18)
N1—N2—C9—S2	−1.4 (3)	C5—C6—C7—C2	−0.3 (4)
C1—C2—C3—C4	179.25 (19)	S2—C10—C11—C12	66.6 (2)
C1—C2—C7—C6	−179.50 (19)	C10—C11—C12—C13	−178.90 (17)
C3—C2—C7—C6	−0.1 (4)	C11—C12—C13—C14	178.41 (17)
C7—C2—C3—C4	−0.2 (4)	C12—C13—C14—C15	178.99 (17)
C2—C3—C4—C5	0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H9···S1i	0.83 (3)	2.56 (3)	3.3760 (19)	168 (2)
C1—H2···Cg1ii	0.98	2.61	3.529 (3)	157

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the C1C6 ring.

DHA	DH	HA	D A	DHA
N2H9S1i	0.83(3)	2.56(3)	3.3760(19)	168(2)
C1H2Cg1ii	0.98	2.61	3.529(3)	157

Symmetry codes: (i) ; (ii) .