Benzyl (E)-3-(4-meth-oxy-benzyl-idene)dithio-carbazate.

The title compound, C(16)H(16)N(2)OS(2), was obtained from a condensation reaction of benzyl dithio-carbazate and 4-meth-oxy-benzaldehyde. In the mol-ecule, the meth-oxy-phenyl ring and dithio-carbazate fragment are located on opposite sides of the C=N double bond, showing an E configuration. The dithio-carbazate fragment is approximately planar (r.m.s. deviation = 0.0052 Å); its mean plane is oriented at dihedral angles of 8.19 (15) and 85.70 (13)°, respectively, to the meth-oxy-phenyl and phenyl rings. Inter-molecular N-H⋯S hydrogen bonds and weak C-H⋯π inter-actions are observed in the crystal structure.

Related literature

For applications of hydrazone and its derivatives in the biological field, see: Okabe et al. (1993 ▶); Hu et al. (2001 ▶). For related structures, see: Shan et al. (2008a ▶,b ▶). For the synthesis, see: Hu et al. (2001 ▶).

Experimental

Crystal data

C16H16N2OS2

M = 316.43

Monoclinic,

a = 10.267 (5) Å

b = 5.150 (2) Å

c = 31.686 (11) Å

β = 97.141 (5)°

V = 1662.4 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 294 K

0.32 × 0.25 × 0.23 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.84, T max = 0.92

6025 measured reflections

2982 independent reflections

1869 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.129

S = 1.04

2982 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.28 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 datablock(s) I, global. DOI: 10.1107/S1600536811042140/xu5352sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042140/xu5352Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042140/xu5352Isup3.cml

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

C16H16N2OS2	F(000) = 664
Mr = 316.43	Dx = 1.264 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2982 reflections
a = 10.267 (5) Å	θ = 3.4–25.2°
b = 5.150 (2) Å	µ = 0.32 mm−1
c = 31.686 (11) Å	T = 294 K
β = 97.141 (5)°	Block, colorless
V = 1662.4 (12) Å3	0.32 × 0.25 × 0.23 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2982 independent reflections
Radiation source: fine-focus sealed tube	1869 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 25.2°, θmin = 3.5°
ω scans	h = −12→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −5→6
Tmin = 0.84, Tmax = 0.92	l = −31→37
6025 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0512P)2] where P = (Fo2 + 2Fc2)/3
2982 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.28 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	0.65124 (8)	0.64526 (18)	0.54959 (2)	0.0628 (3)
S2	0.57408 (9)	0.40404 (17)	0.63003 (2)	0.0631 (3)
O1	−0.0078 (2)	−0.7274 (5)	0.62062 (8)	0.0810 (7)
N1	0.4039 (2)	0.1129 (5)	0.57509 (7)	0.0545 (7)
N2	0.4768 (2)	0.2797 (5)	0.55381 (7)	0.0552 (7)
H2	0.4665	0.2815	0.5265	0.066*
C1	0.2443 (3)	−0.2240 (6)	0.56941 (8)	0.0491 (7)
C2	0.1678 (3)	−0.3916 (6)	0.54309 (9)	0.0582 (9)
H2A	0.1740	−0.3887	0.5141	0.070*
C3	0.0825 (3)	−0.5632 (6)	0.55848 (10)	0.0608 (8)
H3	0.0315	−0.6738	0.5400	0.073*
C4	0.0734 (3)	−0.5699 (6)	0.60140 (10)	0.0572 (8)
C5	0.1509 (3)	−0.4053 (7)	0.62824 (10)	0.0663 (9)
H5	0.1456	−0.4105	0.6573	0.080*
C6	0.2355 (3)	−0.2346 (6)	0.61278 (9)	0.0596 (9)
H6	0.2871	−0.1255	0.6313	0.072*
C7	0.3302 (3)	−0.0417 (6)	0.55184 (9)	0.0553 (8)
H7	0.3314	−0.0376	0.5226	0.066*
C8	0.5635 (3)	0.4391 (6)	0.57512 (8)	0.0498 (8)
C9	0.6968 (4)	0.6468 (7)	0.64781 (9)	0.0725 (10)
H9A	0.7778	0.6104	0.6361	0.087*
H9B	0.6662	0.8177	0.6383	0.087*
C10	0.7200 (5)	0.6388 (8)	0.69529 (11)	0.0815 (12)
C11	0.8198 (6)	0.4920 (11)	0.71552 (14)	0.1309 (19)
H11	0.8712	0.3939	0.6993	0.157*
C12	0.8464 (8)	0.4854 (16)	0.7592 (2)	0.189 (4)
H12	0.9153	0.3870	0.7727	0.226*
C13	0.7687 (13)	0.6270 (17)	0.7815 (2)	0.199 (5)
H13	0.7830	0.6173	0.8110	0.239*
C14	0.6712 (12)	0.7826 (15)	0.7635 (2)	0.212 (5)
H14	0.6231	0.8854	0.7801	0.255*
C15	0.6444 (7)	0.7838 (11)	0.71840 (14)	0.138 (2)
H15	0.5758	0.8830	0.7049	0.166*
C16	−0.0915 (4)	−0.8990 (7)	0.59433 (13)	0.0942 (13)
H16A	−0.1487	−0.7997	0.5741	0.141*
H16B	−0.1431	−0.9991	0.6117	0.141*
H16C	−0.0392	−1.0135	0.5795	0.141*

	U11	U22	U33	U12	U13	U23
S1	0.0604 (6)	0.0731 (6)	0.0556 (5)	−0.0213 (5)	0.0101 (4)	0.0138 (4)
S2	0.0699 (6)	0.0685 (6)	0.0511 (4)	−0.0216 (5)	0.0086 (4)	0.0112 (4)
O1	0.0753 (19)	0.0729 (16)	0.0980 (16)	−0.0258 (14)	0.0229 (14)	0.0156 (14)
N1	0.0472 (16)	0.0563 (16)	0.0604 (14)	−0.0115 (14)	0.0078 (12)	0.0121 (13)
N2	0.0510 (17)	0.0639 (17)	0.0514 (13)	−0.0149 (14)	0.0087 (12)	0.0088 (13)
C1	0.0451 (19)	0.0492 (18)	0.0530 (17)	−0.0071 (15)	0.0060 (14)	0.0066 (14)
C2	0.056 (2)	0.067 (2)	0.0508 (16)	−0.0112 (18)	0.0042 (14)	0.0004 (16)
C3	0.053 (2)	0.058 (2)	0.069 (2)	−0.0126 (17)	−0.0002 (15)	−0.0007 (17)
C4	0.050 (2)	0.0486 (19)	0.074 (2)	−0.0096 (16)	0.0093 (16)	0.0115 (17)
C5	0.074 (2)	0.073 (2)	0.0528 (17)	−0.016 (2)	0.0123 (16)	0.0100 (17)
C6	0.063 (2)	0.060 (2)	0.0542 (18)	−0.0183 (18)	0.0026 (15)	−0.0033 (16)
C7	0.0455 (19)	0.064 (2)	0.0565 (17)	−0.0062 (17)	0.0073 (14)	0.0112 (16)
C8	0.0430 (18)	0.0526 (19)	0.0544 (16)	−0.0034 (15)	0.0088 (14)	0.0089 (15)
C9	0.088 (3)	0.071 (2)	0.0579 (18)	−0.030 (2)	0.0062 (17)	0.0061 (17)
C10	0.120 (4)	0.066 (2)	0.057 (2)	−0.034 (2)	0.006 (2)	0.004 (2)
C11	0.157 (5)	0.132 (4)	0.094 (3)	−0.011 (4)	−0.023 (3)	0.025 (3)
C12	0.271 (10)	0.173 (7)	0.099 (4)	−0.046 (7)	−0.069 (5)	0.040 (5)
C13	0.408 (15)	0.124 (7)	0.064 (4)	−0.114 (8)	0.031 (6)	−0.006 (4)
C14	0.433 (16)	0.110 (6)	0.105 (5)	−0.051 (7)	0.080 (7)	−0.021 (4)
C15	0.228 (7)	0.119 (4)	0.073 (3)	−0.013 (4)	0.040 (4)	−0.005 (3)
C16	0.072 (3)	0.067 (3)	0.145 (3)	−0.028 (2)	0.019 (2)	0.016 (3)

S1—C8	1.665 (3)	C6—H6	0.9300
S2—C8	1.739 (3)	C7—H7	0.9300
S2—C9	1.814 (3)	C9—C10	1.494 (4)
O1—C4	1.360 (4)	C9—H9A	0.9700
O1—C16	1.427 (4)	C9—H9B	0.9700
N1—C7	1.269 (4)	C10—C15	1.356 (6)
N1—N2	1.371 (3)	C10—C11	1.367 (6)
N2—C8	1.331 (3)	C11—C12	1.376 (7)
N2—H2	0.8600	C11—H11	0.9300
C1—C2	1.376 (4)	C12—C13	1.345 (11)
C1—C6	1.390 (4)	C12—H12	0.9300
C1—C7	1.446 (4)	C13—C14	1.352 (13)
C2—C3	1.376 (4)	C13—H13	0.9300
C2—H2A	0.9300	C14—C15	1.423 (8)
C3—C4	1.375 (4)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.381 (4)	C16—H16A	0.9600
C5—C6	1.368 (4)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C8—S2—C9	101.16 (14)	C10—C9—S2	108.1 (2)
C4—O1—C16	117.8 (3)	C10—C9—H9A	110.1
C7—N1—N2	115.5 (2)	S2—C9—H9A	110.1
C8—N2—N1	120.6 (2)	C10—C9—H9B	110.1
C8—N2—H2	119.7	S2—C9—H9B	110.1
N1—N2—H2	119.7	H9A—C9—H9B	108.4
C2—C1—C6	118.2 (3)	C15—C10—C11	119.8 (4)
C2—C1—C7	120.2 (3)	C15—C10—C9	119.9 (4)
C6—C1—C7	121.6 (3)	C11—C10—C9	120.2 (4)
C3—C2—C1	121.9 (3)	C10—C11—C12	121.9 (6)
C3—C2—H2A	119.0	C10—C11—H11	119.1
C1—C2—H2A	119.0	C12—C11—H11	119.1
C4—C3—C2	119.4 (3)	C13—C12—C11	117.3 (8)
C4—C3—H3	120.3	C13—C12—H12	121.3
C2—C3—H3	120.3	C11—C12—H12	121.3
O1—C4—C3	125.3 (3)	C12—C13—C14	123.8 (7)
O1—C4—C5	115.4 (3)	C12—C13—H13	118.1
C3—C4—C5	119.2 (3)	C14—C13—H13	118.1
C6—C5—C4	121.1 (3)	C13—C14—C15	117.8 (8)
C6—C5—H5	119.4	C13—C14—H14	121.1
C4—C5—H5	119.4	C15—C14—H14	121.1
C5—C6—C1	120.1 (3)	C10—C15—C14	119.2 (7)
C5—C6—H6	119.9	C10—C15—H15	120.4
C1—C6—H6	119.9	C14—C15—H15	120.4
N1—C7—C1	122.2 (3)	O1—C16—H16A	109.5
N1—C7—H7	118.9	O1—C16—H16B	109.5
C1—C7—H7	118.9	H16A—C16—H16B	109.5
N2—C8—S1	121.0 (2)	O1—C16—H16C	109.5
N2—C8—S2	113.5 (2)	H16A—C16—H16C	109.5
S1—C8—S2	125.59 (18)	H16B—C16—H16C	109.5

Cg is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1i	0.86	2.59	3.397 (4)	158
C16—H16C···Cgii	0.96	2.83	3.671 (5)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.86	2.59	3.397 (4)	158
C16—H16C⋯Cgii	0.96	2.83	3.671 (5)	147

Symmetry codes: (i) ; (ii) .