Benzyl 3-[(E)-2-nitro-benzyl-idene]dithio-carbazate.

The title compound, C(15)H(13)N(3)O(2)S(2), was obtained from a condensation reaction of benzyl dithio-carbazate and 2-nitro-benzaldehyde. In the mol-ecule, the nearly planar dithio-carbazate fragment [r.m.s deviation = 0.0264 Å] is oriented at dihedral angles of 7.25 (17) and 74.09 (9)°with respect to the two benzene rings. The nitro group is twisted by a dihedral angle of 22.4 (7)° to the attached benzene ring. The nitro-benzene ring and dithio-carbazate fragment are located on the opposite sides of the C=N bond, showing an E configuration. In the crystal, mol-ecules are linked via inter-molecular N-H⋯S hydrogen bonds, forming centrosymmetric supra-molecular dimers. Weak C-H⋯π inter-action is also 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. (2006 ▶, 2008a ▶,b ▶, 2011 ▶). For the synthesis, see: Hu et al. (2001 ▶).

Experimental

Crystal data

C15H13N3O2S2

M = 331.40

Monoclinic,

a = 4.673 (2) Å

b = 28.498 (6) Å

c = 11.735 (5) Å

β = 94.070 (4)°

V = 1558.8 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 294 K

0.38 × 0.25 × 0.23 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.87, T max = 0.94

6957 measured reflections

2814 independent reflections

1925 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.147

S = 1.05

2814 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.47 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/S1600536811028686/xu5268sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028686/xu5268Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028686/xu5268Isup3.cml

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

C15H13N3O2S2	F(000) = 688
Mr = 331.40	Dx = 1.412 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2814 reflections
a = 4.673 (2) Å	θ = 2.7–25.2°
b = 28.498 (6) Å	µ = 0.35 mm−1
c = 11.735 (5) Å	T = 294 K
β = 94.070 (4)°	Needle, yellow
V = 1558.8 (10) Å3	0.38 × 0.25 × 0.23 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2814 independent reflections
Radiation source: fine-focus sealed tube	1925 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 10.0 pixels mm-1	θmax = 25.2°, θmin = 2.8°
ω scans	h = −5→5
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −34→33
Tmin = 0.87, Tmax = 0.94	l = −10→14
6957 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) = 0.147	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0677P)2 + 0.3832P] where P = (Fo2 + 2Fc2)/3
2814 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.47 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	0.1945 (2)	0.55533 (3)	0.40002 (8)	0.0502 (3)
S2	0.53350 (19)	0.50159 (3)	0.23425 (8)	0.0520 (3)
N1	0.3569 (6)	0.42391 (8)	0.3495 (2)	0.0448 (7)
N2	0.2412 (6)	0.46411 (8)	0.3892 (2)	0.0462 (7)
H2	0.1235	0.4627	0.4423	0.055*
N3	0.2496 (8)	0.29447 (12)	0.5248 (3)	0.0760 (10)
O1	0.1632 (9)	0.25714 (11)	0.5505 (3)	0.1173 (13)
O2	0.2227 (15)	0.32692 (14)	0.5852 (5)	0.201 (3)
C1	0.4074 (7)	0.29939 (11)	0.4221 (3)	0.0513 (9)
C2	0.5231 (9)	0.25869 (11)	0.3821 (4)	0.0663 (11)
H2A	0.4958	0.2303	0.4190	0.080*
C3	0.6797 (9)	0.26018 (13)	0.2870 (4)	0.0725 (12)
H3	0.7596	0.2329	0.2595	0.087*
C4	0.7165 (8)	0.30232 (13)	0.2332 (4)	0.0659 (11)
H4	0.8221	0.3036	0.1691	0.079*
C5	0.5979 (8)	0.34250 (11)	0.2739 (3)	0.0539 (9)
H5	0.6260	0.3707	0.2364	0.065*
C6	0.4374 (7)	0.34259 (10)	0.3691 (3)	0.0452 (8)
C7	0.3121 (7)	0.38673 (10)	0.4055 (3)	0.0495 (9)
H7	0.2018	0.3876	0.4684	0.059*
C8	0.3103 (7)	0.50609 (10)	0.3458 (3)	0.0406 (7)
C9	0.5817 (7)	0.56211 (11)	0.1951 (3)	0.0499 (9)
H9A	0.6092	0.5805	0.2646	0.060*
H9B	0.7566	0.5645	0.1556	0.060*
C10	0.3412 (6)	0.58388 (11)	0.1207 (3)	0.0422 (8)
C11	0.2337 (8)	0.56274 (14)	0.0219 (3)	0.0620 (10)
H11	0.3021	0.5334	0.0021	0.074*
C12	0.0259 (9)	0.58440 (18)	−0.0482 (4)	0.0754 (12)
H12	−0.0452	0.5698	−0.1151	0.091*
C13	−0.0762 (9)	0.62724 (17)	−0.0198 (4)	0.0783 (14)
H13	−0.2157	0.6419	−0.0677	0.094*
C14	0.0259 (8)	0.64873 (13)	0.0791 (4)	0.0731 (13)
H14	−0.0454	0.6778	0.0992	0.088*
C15	0.2341 (7)	0.62698 (11)	0.1483 (4)	0.0560 (10)
H15	0.3044	0.6417	0.2152	0.067*

	U11	U22	U33	U12	U13	U23
S1	0.0721 (6)	0.0349 (4)	0.0446 (5)	0.0042 (4)	0.0116 (4)	0.0001 (4)
S2	0.0618 (6)	0.0402 (4)	0.0561 (6)	0.0052 (4)	0.0197 (5)	0.0039 (4)
N1	0.0575 (16)	0.0352 (14)	0.0415 (16)	0.0028 (12)	0.0008 (14)	0.0020 (13)
N2	0.0601 (16)	0.0347 (14)	0.0451 (17)	0.0064 (12)	0.0132 (14)	0.0034 (13)
N3	0.107 (3)	0.0466 (19)	0.076 (3)	0.0025 (19)	0.019 (2)	0.0149 (19)
O1	0.170 (4)	0.076 (2)	0.110 (3)	−0.038 (2)	0.042 (3)	0.023 (2)
O2	0.406 (9)	0.068 (2)	0.152 (4)	0.020 (4)	0.178 (5)	0.029 (3)
C1	0.059 (2)	0.0388 (18)	0.055 (2)	−0.0062 (15)	−0.0015 (18)	0.0084 (17)
C2	0.080 (3)	0.0318 (17)	0.085 (3)	−0.0018 (17)	−0.009 (2)	0.008 (2)
C3	0.088 (3)	0.041 (2)	0.088 (3)	0.0135 (19)	0.006 (3)	−0.006 (2)
C4	0.081 (3)	0.055 (2)	0.063 (3)	0.0091 (19)	0.012 (2)	−0.002 (2)
C5	0.068 (2)	0.0364 (17)	0.057 (2)	0.0012 (16)	0.005 (2)	0.0052 (17)
C6	0.0516 (19)	0.0356 (16)	0.047 (2)	−0.0011 (14)	−0.0061 (17)	0.0048 (15)
C7	0.066 (2)	0.0368 (17)	0.046 (2)	−0.0010 (16)	0.0056 (18)	0.0076 (16)
C8	0.0456 (17)	0.0395 (16)	0.0358 (18)	0.0000 (13)	−0.0041 (15)	0.0037 (14)
C9	0.0454 (18)	0.0479 (18)	0.057 (2)	−0.0060 (15)	0.0100 (17)	0.0089 (17)
C10	0.0396 (17)	0.0466 (18)	0.041 (2)	−0.0072 (14)	0.0089 (15)	0.0093 (16)
C11	0.064 (2)	0.075 (2)	0.048 (2)	−0.001 (2)	0.014 (2)	−0.007 (2)
C12	0.073 (3)	0.111 (4)	0.041 (2)	−0.020 (3)	−0.001 (2)	0.003 (2)
C13	0.057 (2)	0.090 (3)	0.085 (4)	−0.010 (2)	−0.009 (2)	0.048 (3)
C14	0.067 (3)	0.047 (2)	0.103 (4)	−0.0021 (19)	−0.009 (3)	0.018 (2)
C15	0.060 (2)	0.0395 (18)	0.067 (3)	−0.0069 (16)	−0.006 (2)	0.0060 (18)

S1—C8	1.648 (3)	C5—C6	1.389 (5)
S2—C8	1.735 (3)	C5—H5	0.9300
S2—C9	1.803 (3)	C6—C7	1.464 (4)
N1—C7	1.272 (4)	C7—H7	0.9300
N1—N2	1.363 (3)	C9—C10	1.507 (5)
N2—C8	1.349 (4)	C9—H9A	0.9700
N2—H2	0.8600	C9—H9B	0.9700
N3—O2	1.178 (5)	C10—C11	1.370 (5)
N3—O1	1.185 (4)	C10—C15	1.374 (5)
N3—C1	1.464 (5)	C11—C12	1.374 (6)
C1—C2	1.376 (5)	C11—H11	0.9300
C1—C6	1.390 (4)	C12—C13	1.361 (6)
C2—C3	1.377 (6)	C12—H12	0.9300
C2—H2A	0.9300	C13—C14	1.368 (6)
C3—C4	1.373 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.370 (5)
C4—C5	1.373 (5)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
C8—S2—C9	102.38 (15)	C6—C7—H7	120.6
C7—N1—N2	116.1 (3)	N2—C8—S1	121.0 (2)
C8—N2—N1	120.3 (3)	N2—C8—S2	113.1 (2)
C8—N2—H2	119.8	S1—C8—S2	125.83 (18)
N1—N2—H2	119.8	C10—C9—S2	116.1 (2)
O2—N3—O1	119.9 (4)	C10—C9—H9A	108.3
O2—N3—C1	120.2 (4)	S2—C9—H9A	108.3
O1—N3—C1	119.8 (4)	C10—C9—H9B	108.3
C2—C1—C6	122.6 (4)	S2—C9—H9B	108.3
C2—C1—N3	115.7 (3)	H9A—C9—H9B	107.4
C6—C1—N3	121.7 (3)	C11—C10—C15	118.3 (3)
C1—C2—C3	119.6 (4)	C11—C10—C9	121.5 (3)
C1—C2—H2A	120.2	C15—C10—C9	120.1 (3)
C3—C2—H2A	120.2	C10—C11—C12	120.7 (4)
C4—C3—C2	119.4 (4)	C10—C11—H11	119.7
C4—C3—H3	120.3	C12—C11—H11	119.7
C2—C3—H3	120.3	C13—C12—C11	120.1 (4)
C5—C4—C3	120.2 (4)	C13—C12—H12	119.9
C5—C4—H4	119.9	C11—C12—H12	119.9
C3—C4—H4	119.9	C12—C13—C14	120.2 (4)
C4—C5—C6	122.4 (3)	C12—C13—H13	119.9
C4—C5—H5	118.8	C14—C13—H13	119.9
C6—C5—H5	118.8	C13—C14—C15	119.4 (4)
C5—C6—C1	115.8 (3)	C13—C14—H14	120.3
C5—C6—C7	119.1 (3)	C15—C14—H14	120.3
C1—C6—C7	125.1 (3)	C14—C15—C10	121.3 (4)
N1—C7—C6	118.8 (3)	C14—C15—H15	119.3
N1—C7—H7	120.6	C10—C15—H15	119.3

Cg is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1i	0.86	2.51	3.359 (3)	171
C9—H9B···Cgii	0.97	2.50	3.410 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.86	2.51	3.359 (3)	171
C9—H9B⋯Cgii	0.97	2.50	3.410 (4)	156

Symmetry codes: (i) ; (ii) .