Benzyl (E)-3-(2-methyl-benzyl-idene)dithio-carbazate.

The title compound, C(16)H(16)N(2)S(2), was obtained from the condensation reaction of benzyl dithio-carbazate and 2-methyl-benzaldehyde. The asymmetric unit contains two independent mol-ecules. In both mol-ecules, the methyl-phenyl ring and the dithio-carbazate fragment are located on opposite sides of the C=N bond, showing an E conformation. In each mol-ecule, the dithio-carbazate fragment is approximately planar, the r.m.s deviations being 0.018 and 0.025 Å. The mean plane of dithio-carbazate group is oriented at dihedral angles of 7.9 (3) and 68.24 (12)°, respectively, to the methyl-phenyl and phenyl rings in one mol-ecule, while the corresponding angles in the other mol-ecule are 10.9 (3) and 69.76 (16)°. Inter-molecular N-H⋯S hydrogen bonding occurs in the crystal structure to generate inversion dimers for both molecules.

Related literature

For potential 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. (2006 ▶, 2008a ▶,b ▶, 2011 ▶). For the synthesis, see: Hu et al. (2001 ▶).

Experimental

Crystal data

C16H16N2S2

M = 300.43

Monoclinic,

a = 21.976 (7) Å

b = 6.126 (3) Å

c = 23.099 (6) Å

β = 90.840 (4)°

V = 3109 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 294 K

0.29 × 0.23 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.85, T max = 0.93

11281 measured reflections

5596 independent reflections

2739 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.162

S = 1.02

5596 reflections

363 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.19 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO (Rigaku, 1998 ▶); 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/S1600536811033113/xu5276sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033113/xu5276Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033113/xu5276Isup3.cml

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

C16H16N2S2	F(000) = 1264
Mr = 300.43	Dx = 1.284 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5596 reflections
a = 21.976 (7) Å	θ = 3.3–25.2°
b = 6.126 (3) Å	µ = 0.33 mm−1
c = 23.099 (6) Å	T = 294 K
β = 90.840 (4)°	Block, yellow
V = 3109 (2) Å3	0.29 × 0.23 × 0.18 mm
Z = 8

Rigaku R-AXIS RAPID IP diffractometer	5596 independent reflections
Radiation source: fine-focus sealed tube	2739 reflections with I > 2σ(I)
graphite	Rint = 0.055
Detector resolution: 10.0 pixels mm-1	θmax = 25.2°, θmin = 3.4°
ω scans	h = −25→26
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −6→7
Tmin = 0.85, Tmax = 0.93	l = −18→27
11281 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0432P)2] where P = (Fo2 + 2Fc2)/3
5596 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.19 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	0.00768 (5)	0.7325 (2)	0.57333 (6)	0.0829 (5)
S2	0.12246 (5)	0.58916 (18)	0.63604 (5)	0.0611 (4)
S3	0.42020 (6)	0.2494 (2)	0.49716 (6)	0.0866 (5)
S4	0.35943 (5)	0.34105 (19)	0.38154 (6)	0.0652 (4)
N1	0.12405 (14)	0.2604 (6)	0.55431 (16)	0.0584 (10)
N2	0.07408 (15)	0.3932 (6)	0.54827 (17)	0.0663 (11)
H2N	0.0474	0.3656	0.5217	0.080*
N3	0.44164 (15)	0.6850 (6)	0.37635 (17)	0.0599 (10)
N4	0.44538 (15)	0.5710 (6)	0.42774 (18)	0.0686 (11)
H4N	0.4702	0.6145	0.4544	0.082*
C1	0.17913 (18)	−0.0439 (6)	0.51748 (19)	0.0538 (11)
C2	0.1794 (2)	−0.2255 (8)	0.4810 (2)	0.0660 (12)
C3	0.2286 (3)	−0.3619 (9)	0.4846 (3)	0.0940 (18)
H3	0.2294	−0.4847	0.4610	0.113*
C4	0.2768 (3)	−0.3257 (9)	0.5215 (3)	0.0915 (18)
H4	0.3094	−0.4223	0.5228	0.110*
C5	0.2763 (2)	−0.1464 (9)	0.5561 (2)	0.0819 (16)
H5	0.3091	−0.1190	0.5810	0.098*
C6	0.22812 (18)	−0.0064 (7)	0.5549 (2)	0.0667 (13)
H6	0.2280	0.1148	0.5791	0.080*
C7	0.12811 (18)	0.1054 (7)	0.5170 (2)	0.0583 (12)
H7	0.0976	0.0889	0.4890	0.070*
C8	0.1282 (2)	−0.2723 (8)	0.4390 (2)	0.0920 (18)
H8A	0.1301	−0.1726	0.4071	0.138*
H8B	0.0900	−0.2550	0.4582	0.138*
H8C	0.1316	−0.4193	0.4251	0.138*
C9	0.06632 (17)	0.5648 (6)	0.58315 (19)	0.0535 (11)
C10	0.0965 (2)	0.8266 (7)	0.6743 (2)	0.0695 (14)
H10A	0.0980	0.9532	0.6492	0.083*
H10B	0.0547	0.8056	0.6860	0.083*
C11	0.13608 (16)	0.8637 (7)	0.72670 (19)	0.0491 (10)
C12	0.17184 (18)	1.0460 (7)	0.7309 (2)	0.0603 (12)
H12	0.1729	1.1440	0.7002	0.072*
C13	0.2064 (2)	1.0868 (8)	0.7802 (3)	0.0735 (15)
H13	0.2300	1.2126	0.7828	0.088*
C14	0.2058 (2)	0.9446 (9)	0.8243 (2)	0.0819 (16)
H14	0.2294	0.9705	0.8574	0.098*
C15	0.1703 (2)	0.7607 (9)	0.8206 (2)	0.0826 (15)
H15	0.1699	0.6613	0.8510	0.099*
C16	0.13541 (19)	0.7239 (7)	0.7718 (2)	0.0659 (13)
H16	0.1109	0.6004	0.7698	0.079*
C17	0.48183 (18)	0.9804 (7)	0.3223 (2)	0.0614 (13)
C18	0.51708 (19)	1.1720 (8)	0.3223 (3)	0.0715 (14)
C19	0.5172 (2)	1.2945 (8)	0.2726 (3)	0.0870 (18)
H19	0.5399	1.4227	0.2723	0.104*
C20	0.4858 (3)	1.2379 (11)	0.2236 (3)	0.108 (2)
H20	0.4871	1.3264	0.1909	0.130*
C21	0.4525 (2)	1.0512 (10)	0.2228 (3)	0.102 (2)
H21	0.4316	1.0090	0.1893	0.123*
C22	0.4500 (2)	0.9238 (8)	0.2725 (2)	0.0798 (15)
H22	0.4263	0.7980	0.2723	0.096*
C23	0.4788 (2)	0.8437 (7)	0.3726 (2)	0.0664 (14)
H23	0.5049	0.8723	0.4038	0.080*
C24	0.5559 (2)	1.2373 (8)	0.3736 (3)	0.097 (2)
H24A	0.5888	1.1352	0.3783	0.145*
H24B	0.5317	1.2375	0.4078	0.145*
H24C	0.5721	1.3808	0.3673	0.145*
C25	0.41069 (17)	0.3917 (7)	0.43703 (19)	0.0565 (12)
C26	0.31883 (18)	0.1063 (7)	0.4079 (2)	0.0691 (14)
H26A	0.3464	−0.0166	0.4119	0.083*
H26B	0.3022	0.1380	0.4457	0.083*
C27	0.26839 (18)	0.0506 (7)	0.3661 (2)	0.0606 (12)
C28	0.2196 (2)	0.1840 (9)	0.3593 (3)	0.103 (2)
H28	0.2176	0.3112	0.3811	0.123*
C29	0.1729 (3)	0.1357 (12)	0.3207 (3)	0.120 (3)
H29	0.1400	0.2301	0.3168	0.144*
C30	0.1750 (3)	−0.0472 (11)	0.2887 (3)	0.0939 (18)
H30	0.1434	−0.0817	0.2631	0.113*
C31	0.2229 (3)	−0.1785 (8)	0.2943 (2)	0.0888 (17)
H31	0.2249	−0.3045	0.2719	0.107*
C32	0.2703 (2)	−0.1306 (8)	0.3329 (2)	0.0776 (15)
H32	0.3035	−0.2243	0.3359	0.093*

	U11	U22	U33	U12	U13	U23
S1	0.0705 (8)	0.0936 (9)	0.0833 (11)	0.0323 (7)	−0.0394 (8)	−0.0285 (8)
S2	0.0568 (6)	0.0694 (8)	0.0564 (8)	0.0151 (6)	−0.0207 (6)	−0.0124 (6)
S3	0.0834 (8)	0.1052 (11)	0.0703 (10)	−0.0175 (8)	−0.0289 (8)	0.0303 (8)
S4	0.0670 (7)	0.0727 (8)	0.0554 (8)	0.0018 (6)	−0.0150 (6)	0.0100 (6)
N1	0.0523 (19)	0.061 (2)	0.061 (3)	0.0101 (18)	−0.0145 (19)	−0.003 (2)
N2	0.060 (2)	0.069 (2)	0.070 (3)	0.0154 (19)	−0.027 (2)	−0.017 (2)
N3	0.065 (2)	0.058 (2)	0.056 (3)	−0.0019 (19)	−0.0104 (19)	0.015 (2)
N4	0.066 (2)	0.076 (3)	0.063 (3)	−0.003 (2)	−0.016 (2)	0.007 (2)
C1	0.062 (2)	0.050 (2)	0.049 (3)	0.013 (2)	−0.005 (2)	0.001 (2)
C2	0.078 (3)	0.075 (3)	0.044 (3)	0.010 (3)	0.001 (2)	−0.007 (3)
C3	0.116 (4)	0.086 (4)	0.080 (5)	0.032 (4)	0.005 (4)	−0.026 (3)
C4	0.096 (4)	0.093 (4)	0.086 (5)	0.034 (3)	0.005 (4)	−0.013 (4)
C5	0.067 (3)	0.098 (4)	0.080 (4)	0.016 (3)	−0.015 (3)	0.001 (3)
C6	0.063 (3)	0.071 (3)	0.065 (4)	0.012 (2)	−0.018 (2)	−0.011 (2)
C7	0.064 (3)	0.059 (3)	0.052 (3)	0.002 (2)	−0.014 (2)	−0.006 (2)
C8	0.116 (4)	0.096 (4)	0.063 (4)	0.005 (3)	−0.027 (3)	−0.026 (3)
C9	0.053 (2)	0.059 (3)	0.047 (3)	0.009 (2)	−0.016 (2)	−0.005 (2)
C10	0.072 (3)	0.075 (3)	0.061 (3)	0.019 (2)	−0.025 (3)	−0.021 (3)
C11	0.047 (2)	0.053 (2)	0.047 (3)	0.002 (2)	−0.004 (2)	0.001 (2)
C12	0.066 (3)	0.055 (3)	0.060 (3)	0.004 (2)	0.003 (2)	0.007 (2)
C13	0.066 (3)	0.065 (3)	0.088 (4)	−0.008 (3)	−0.011 (3)	−0.016 (3)
C14	0.079 (3)	0.094 (4)	0.071 (4)	0.003 (3)	−0.022 (3)	−0.020 (3)
C15	0.098 (4)	0.087 (4)	0.062 (4)	0.002 (3)	−0.009 (3)	0.016 (3)
C16	0.065 (3)	0.070 (3)	0.063 (3)	−0.017 (2)	−0.013 (3)	0.003 (3)
C17	0.057 (2)	0.058 (3)	0.069 (4)	0.009 (2)	−0.007 (2)	0.009 (3)
C18	0.047 (2)	0.065 (3)	0.103 (5)	0.000 (2)	0.016 (3)	0.005 (3)
C19	0.063 (3)	0.070 (4)	0.130 (6)	−0.013 (3)	0.022 (3)	0.020 (4)
C20	0.092 (4)	0.117 (5)	0.116 (6)	−0.018 (4)	0.007 (4)	0.042 (4)
C21	0.103 (4)	0.124 (5)	0.079 (5)	−0.027 (4)	−0.019 (4)	0.028 (4)
C22	0.088 (3)	0.078 (3)	0.072 (4)	−0.016 (3)	−0.009 (3)	0.014 (3)
C23	0.061 (3)	0.063 (3)	0.074 (4)	0.002 (2)	−0.017 (3)	0.001 (3)
C24	0.066 (3)	0.084 (4)	0.141 (6)	−0.013 (3)	−0.001 (4)	−0.021 (4)
C25	0.050 (2)	0.062 (3)	0.057 (3)	0.010 (2)	−0.007 (2)	0.008 (2)
C26	0.065 (3)	0.072 (3)	0.071 (4)	−0.003 (2)	−0.012 (3)	0.016 (3)
C27	0.059 (2)	0.061 (3)	0.062 (3)	0.006 (2)	−0.011 (2)	0.003 (3)
C28	0.102 (4)	0.112 (4)	0.093 (5)	0.044 (4)	−0.046 (4)	−0.045 (4)
C29	0.097 (4)	0.151 (6)	0.111 (6)	0.044 (4)	−0.053 (4)	−0.036 (5)
C30	0.082 (4)	0.123 (5)	0.076 (5)	−0.013 (4)	−0.013 (3)	−0.007 (4)
C31	0.120 (4)	0.069 (3)	0.077 (4)	−0.016 (3)	−0.006 (4)	−0.024 (3)
C32	0.086 (3)	0.061 (3)	0.085 (4)	0.008 (3)	0.000 (3)	0.000 (3)

S1—C9	1.661 (4)	C13—C14	1.341 (7)
S2—C9	1.730 (4)	C13—H13	0.9300
S2—C10	1.800 (4)	C14—C15	1.372 (6)
S3—C25	1.651 (4)	C14—H14	0.9300
S4—C25	1.722 (4)	C15—C16	1.372 (6)
S4—C26	1.803 (4)	C15—H15	0.9300
N1—C7	1.287 (5)	C16—H16	0.9300
N1—N2	1.372 (4)	C17—C22	1.381 (6)
N2—C9	1.337 (5)	C17—C18	1.406 (6)
N2—H2N	0.8600	C17—C23	1.436 (6)
N3—C23	1.273 (5)	C18—C19	1.372 (7)
N3—N4	1.378 (5)	C18—C24	1.503 (7)
N4—C25	1.356 (5)	C19—C20	1.362 (7)
N4—H4N	0.8600	C19—H19	0.9300
C1—C6	1.390 (5)	C20—C21	1.357 (7)
C1—C2	1.396 (6)	C20—H20	0.9300
C1—C7	1.447 (5)	C21—C22	1.391 (7)
C2—C3	1.370 (6)	C21—H21	0.9300
C2—C8	1.502 (5)	C22—H22	0.9300
C3—C4	1.366 (6)	C23—H23	0.9300
C3—H3	0.9300	C24—H24A	0.9600
C4—C5	1.360 (7)	C24—H24B	0.9600
C4—H4	0.9300	C24—H24C	0.9600
C5—C6	1.362 (6)	C26—C27	1.500 (5)
C5—H5	0.9300	C26—H26A	0.9700
C6—H6	0.9300	C26—H26B	0.9700
C7—H7	0.9300	C27—C32	1.350 (6)
C8—H8A	0.9600	C27—C28	1.355 (6)
C8—H8B	0.9600	C28—C29	1.383 (6)
C8—H8C	0.9600	C28—H28	0.9300
C10—C11	1.497 (5)	C29—C30	1.343 (7)
C10—H10A	0.9700	C29—H29	0.9300
C10—H10B	0.9700	C30—C31	1.330 (7)
C11—C16	1.350 (6)	C30—H30	0.9300
C11—C12	1.368 (5)	C31—C32	1.391 (6)
C12—C13	1.381 (6)	C31—H31	0.9300
C12—H12	0.9300	C32—H32	0.9300
C9—S2—C10	100.88 (18)	C14—C15—H15	120.1
C25—S4—C26	102.3 (2)	C16—C15—H15	120.1
C7—N1—N2	115.6 (3)	C11—C16—C15	121.2 (4)
C9—N2—N1	120.9 (3)	C11—C16—H16	119.4
C9—N2—H2N	119.5	C15—C16—H16	119.4
N1—N2—H2N	119.5	C22—C17—C18	118.9 (5)
C23—N3—N4	114.5 (4)	C22—C17—C23	119.9 (4)
C25—N4—N3	121.3 (3)	C18—C17—C23	121.2 (4)
C25—N4—H4N	119.3	C19—C18—C17	117.6 (5)
N3—N4—H4N	119.3	C19—C18—C24	120.4 (5)
C6—C1—C2	119.9 (4)	C17—C18—C24	121.9 (5)
C6—C1—C7	119.6 (4)	C20—C19—C18	123.3 (5)
C2—C1—C7	120.6 (4)	C20—C19—H19	118.4
C3—C2—C1	117.3 (4)	C18—C19—H19	118.4
C3—C2—C8	120.5 (5)	C21—C20—C19	119.5 (6)
C1—C2—C8	122.2 (4)	C21—C20—H20	120.2
C4—C3—C2	122.9 (5)	C19—C20—H20	120.2
C4—C3—H3	118.5	C20—C21—C22	119.3 (5)
C2—C3—H3	118.5	C20—C21—H21	120.4
C5—C4—C3	119.0 (5)	C22—C21—H21	120.4
C5—C4—H4	120.5	C17—C22—C21	121.4 (5)
C3—C4—H4	120.5	C17—C22—H22	119.3
C4—C5—C6	120.6 (5)	C21—C22—H22	119.3
C4—C5—H5	119.7	N3—C23—C17	122.5 (4)
C6—C5—H5	119.7	N3—C23—H23	118.7
C5—C6—C1	120.2 (4)	C17—C23—H23	118.7
C5—C6—H6	119.9	C18—C24—H24A	109.5
C1—C6—H6	119.9	C18—C24—H24B	109.5
N1—C7—C1	121.5 (4)	H24A—C24—H24B	109.5
N1—C7—H7	119.3	C18—C24—H24C	109.5
C1—C7—H7	119.3	H24A—C24—H24C	109.5
C2—C8—H8A	109.5	H24B—C24—H24C	109.5
C2—C8—H8B	109.5	N4—C25—S3	119.8 (3)
H8A—C8—H8B	109.5	N4—C25—S4	113.0 (3)
C2—C8—H8C	109.5	S3—C25—S4	127.2 (3)
H8A—C8—H8C	109.5	C27—C26—S4	109.2 (3)
H8B—C8—H8C	109.5	C27—C26—H26A	109.8
N2—C9—S1	120.6 (3)	S4—C26—H26A	109.8
N2—C9—S2	113.4 (3)	C27—C26—H26B	109.8
S1—C9—S2	126.0 (3)	S4—C26—H26B	109.8
C11—C10—S2	109.6 (3)	H26A—C26—H26B	108.3
C11—C10—H10A	109.8	C32—C27—C28	117.4 (4)
S2—C10—H10A	109.8	C32—C27—C26	121.7 (4)
C11—C10—H10B	109.8	C28—C27—C26	120.9 (4)
S2—C10—H10B	109.8	C27—C28—C29	121.6 (5)
H10A—C10—H10B	108.2	C27—C28—H28	119.2
C16—C11—C12	118.4 (4)	C29—C28—H28	119.2
C16—C11—C10	121.0 (4)	C30—C29—C28	120.1 (5)
C12—C11—C10	120.5 (4)	C30—C29—H29	119.9
C11—C12—C13	121.0 (4)	C28—C29—H29	119.9
C11—C12—H12	119.5	C31—C30—C29	119.0 (5)
C13—C12—H12	119.5	C31—C30—H30	120.5
C14—C13—C12	119.8 (4)	C29—C30—H30	120.5
C14—C13—H13	120.1	C30—C31—C32	121.2 (5)
C12—C13—H13	120.1	C30—C31—H31	119.4
C13—C14—C15	119.8 (5)	C32—C31—H31	119.4
C13—C14—H14	120.1	C27—C32—C31	120.6 (5)
C15—C14—H14	120.1	C27—C32—H32	119.7
C14—C15—C16	119.8 (5)	C31—C32—H32	119.7

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···S1i	0.86	2.56	3.400 (4)	165
N4—H4N···S3ii	0.86	2.77	3.577 (4)	157

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	3.400 (4)	165
N4—H4N⋯S3ii	0.86	2.77	3.577 (4)	157

Symmetry codes: (i) ; (ii) .