Benzyl 3-[(E)-benzyl-idene]dithio-carbazate.

Crystals of the title compound, C(15)H(14)N(2)S(2), were obtained from a condensation reaction of benzyl dithio-carbazate and benzaldehyde. The mol-ecule assumes an E configuration about the N=C double bond. The phenyl ring of the thio-ester group is nearly perpendicular to the dithio-carbazate plane, with a dihedral angle of 84.60 (5)°. In the crystal structure, inter-molecular N-H⋯S hydrogen bonding links adjacent mol-ecules to form a centrosymmetric supra-molecular dimer.

Related literature

For general background, see: Okabe et al. (1993 ▶); Hu et al. (2001 ▶). For related structures, see: Shan et al. (2006 ▶, 2008 ▶); Zhang et al. (2005 ▶). For synthesis, see: Hu et al. (2001 ▶).

Experimental

Crystal data

C15H14N2S2

M = 286.40

Monoclinic,

a = 5.0053 (18) Å

b = 23.075 (8) Å

c = 12.646 (5) Å

β = 97.652 (12)°

V = 1447.6 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 295 (2) K

0.30 × 0.28 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: none

15395 measured reflections

2653 independent reflections

2115 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.087

S = 1.05

2653 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.18 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/S1600536808012944/xu2422sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012944/xu2422Isup2.hkl

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

C15H14N2S2	F000 = 600
Mr = 286.40	Dx = 1.314 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6568 reflections
a = 5.0053 (18) Å	θ = 1.9–25.0º
b = 23.075 (8) Å	µ = 0.36 mm−1
c = 12.646 (5) Å	T = 295 (2) K
β = 97.652 (12)º	Prism, yellow
V = 1447.6 (9) Å3	0.30 × 0.28 × 0.22 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2653 independent reflections
Radiation source: fine-focus sealed tube	2115 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.034
Detector resolution: 10.00 pixels mm-1	θmax = 25.5º
T = 295(2) K	θmin = 1.8º
ω scans	h = −5→6
Absorption correction: none	k = −27→27
15395 measured reflections	l = −15→13

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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0424P)2 + 0.226P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2653 reflections	Δρmax = 0.15 e Å−3
172 parameters	Δρmin = −0.18 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	−0.16273 (11)	0.58470 (2)	0.94815 (4)	0.06114 (17)
S2	0.02011 (10)	0.602875 (18)	0.73176 (4)	0.05159 (15)
N1	0.3232 (3)	0.50304 (6)	0.78197 (11)	0.0493 (4)
N2	0.1740 (3)	0.51871 (6)	0.86146 (11)	0.0516 (4)
H2N	0.1829	0.4979	0.9183	0.062*
C1	0.6444 (3)	0.43585 (7)	0.72802 (14)	0.0486 (4)
C2	0.6602 (4)	0.46157 (8)	0.62992 (16)	0.0599 (5)
H2	0.5621	0.4951	0.6109	0.072*
C3	0.8199 (5)	0.43796 (10)	0.56054 (17)	0.0721 (6)
H3	0.8285	0.4554	0.4948	0.087*
C4	0.9663 (4)	0.38875 (10)	0.5882 (2)	0.0764 (6)
H4	1.0736	0.3728	0.5411	0.092*
C5	0.9551 (4)	0.36326 (10)	0.68450 (19)	0.0766 (6)
H5	1.0555	0.3300	0.7029	0.092*
C6	0.7955 (4)	0.38637 (8)	0.75514 (17)	0.0632 (5)
H6	0.7894	0.3687	0.8209	0.076*
C7	0.4749 (4)	0.45888 (7)	0.80289 (15)	0.0529 (4)
H7	0.4769	0.4407	0.8687	0.064*
C8	0.0160 (3)	0.56550 (7)	0.85190 (13)	0.0458 (4)
C9	−0.2180 (4)	0.66100 (7)	0.74434 (14)	0.0531 (4)
H9A	−0.3989	0.6455	0.7419	0.064*
H9B	−0.1716	0.6810	0.8117	0.064*
C10	−0.2041 (4)	0.70207 (7)	0.65275 (14)	0.0494 (4)
C11	−0.3930 (4)	0.69963 (9)	0.56287 (17)	0.0667 (5)
H11	−0.5313	0.6725	0.5594	0.080*
C12	−0.3804 (5)	0.73660 (11)	0.47831 (19)	0.0829 (7)
H12	−0.5085	0.7340	0.4181	0.099*
C13	−0.1794 (5)	0.77726 (10)	0.4826 (2)	0.0791 (7)
H13	−0.1727	0.8028	0.4261	0.095*
C14	0.0112 (5)	0.77991 (9)	0.5708 (2)	0.0763 (6)
H14	0.1498	0.8069	0.5738	0.092*
C15	−0.0015 (4)	0.74263 (8)	0.65529 (17)	0.0646 (5)
H15	0.1288	0.7449	0.7149	0.077*

	U11	U22	U33	U12	U13	U23
S1	0.0859 (4)	0.0527 (3)	0.0517 (3)	0.0075 (2)	0.0347 (3)	0.0005 (2)
S2	0.0620 (3)	0.0500 (3)	0.0471 (3)	0.00360 (19)	0.0232 (2)	0.00234 (19)
N1	0.0549 (9)	0.0477 (8)	0.0489 (8)	−0.0014 (7)	0.0201 (7)	−0.0032 (6)
N2	0.0653 (9)	0.0477 (8)	0.0461 (8)	0.0036 (7)	0.0230 (7)	0.0024 (6)
C1	0.0480 (10)	0.0471 (9)	0.0524 (11)	−0.0032 (7)	0.0134 (8)	−0.0040 (8)
C2	0.0651 (12)	0.0590 (10)	0.0583 (12)	0.0062 (9)	0.0185 (10)	0.0013 (9)
C3	0.0781 (15)	0.0856 (15)	0.0573 (13)	0.0032 (12)	0.0262 (11)	−0.0024 (11)
C4	0.0655 (14)	0.0940 (16)	0.0730 (16)	0.0107 (12)	0.0213 (11)	−0.0231 (13)
C5	0.0759 (15)	0.0712 (13)	0.0842 (17)	0.0250 (11)	0.0162 (12)	−0.0062 (12)
C6	0.0666 (13)	0.0602 (11)	0.0645 (13)	0.0083 (9)	0.0144 (10)	0.0046 (9)
C7	0.0610 (11)	0.0505 (9)	0.0502 (11)	0.0008 (8)	0.0179 (9)	0.0027 (8)
C8	0.0546 (10)	0.0411 (8)	0.0442 (10)	−0.0077 (7)	0.0156 (8)	−0.0042 (7)
C9	0.0545 (11)	0.0533 (10)	0.0550 (11)	0.0019 (8)	0.0197 (9)	−0.0007 (8)
C10	0.0528 (10)	0.0460 (9)	0.0519 (11)	0.0087 (8)	0.0166 (8)	−0.0021 (8)
C11	0.0584 (12)	0.0711 (13)	0.0704 (14)	0.0066 (10)	0.0081 (10)	0.0072 (11)
C12	0.0804 (16)	0.0956 (17)	0.0710 (15)	0.0220 (14)	0.0040 (12)	0.0202 (13)
C13	0.0980 (18)	0.0725 (14)	0.0732 (16)	0.0309 (13)	0.0347 (14)	0.0260 (12)
C14	0.0918 (17)	0.0560 (11)	0.0876 (17)	−0.0046 (11)	0.0362 (14)	0.0068 (11)
C15	0.0734 (13)	0.0599 (11)	0.0619 (13)	−0.0063 (10)	0.0146 (10)	−0.0004 (9)

S1—C8	1.6636 (17)	C5—H5	0.9300
S2—C8	1.7495 (17)	C6—H6	0.9300
S2—C9	1.8153 (18)	C7—H7	0.9300
N1—C7	1.277 (2)	C9—C10	1.505 (2)
N1—N2	1.3777 (19)	C9—H9A	0.9700
N2—C8	1.334 (2)	C9—H9B	0.9700
N2—H2N	0.8600	C10—C15	1.377 (3)
C1—C2	1.387 (3)	C10—C11	1.379 (3)
C1—C6	1.387 (3)	C11—C12	1.376 (3)
C1—C7	1.454 (2)	C11—H11	0.9300
C2—C3	1.375 (3)	C12—C13	1.371 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.372 (3)	C13—C14	1.370 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.360 (3)	C14—C15	1.380 (3)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.382 (3)	C15—H15	0.9300
C8—S2—C9	101.79 (8)	N2—C8—S2	113.71 (12)
C7—N1—N2	115.03 (14)	S1—C8—S2	125.02 (10)
C8—N2—N1	121.23 (14)	C10—C9—S2	107.43 (11)
C8—N2—H2N	119.4	C10—C9—H9A	110.2
N1—N2—H2N	119.4	S2—C9—H9A	110.2
C2—C1—C6	118.64 (17)	C10—C9—H9B	110.2
C2—C1—C7	122.28 (16)	S2—C9—H9B	110.2
C6—C1—C7	119.08 (17)	H9A—C9—H9B	108.5
C3—C2—C1	120.55 (19)	C15—C10—C11	117.96 (18)
C3—C2—H2	119.7	C15—C10—C9	121.28 (17)
C1—C2—H2	119.7	C11—C10—C9	120.75 (17)
C4—C3—C2	120.1 (2)	C12—C11—C10	121.2 (2)
C4—C3—H3	120.0	C12—C11—H11	119.4
C2—C3—H3	120.0	C10—C11—H11	119.4
C5—C4—C3	120.2 (2)	C13—C12—C11	120.2 (2)
C5—C4—H4	119.9	C13—C12—H12	119.9
C3—C4—H4	119.9	C11—C12—H12	119.9
C4—C5—C6	120.5 (2)	C14—C13—C12	119.4 (2)
C4—C5—H5	119.7	C14—C13—H13	120.3
C6—C5—H5	119.7	C12—C13—H13	120.3
C5—C6—C1	120.0 (2)	C13—C14—C15	120.3 (2)
C5—C6—H6	120.0	C13—C14—H14	119.9
C1—C6—H6	120.0	C15—C14—H14	119.9
N1—C7—C1	122.63 (16)	C10—C15—C14	121.0 (2)
N1—C7—H7	118.7	C10—C15—H15	119.5
C1—C7—H7	118.7	C14—C15—H15	119.5
N2—C8—S1	121.27 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···S1i	0.86	2.56	3.396 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯S1i	0.86	2.56	3.396 (2)	165

Symmetry code: (i) .