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

In the title compound, C(15)H(13)N(3)O(2)S(2), the dihedral angle between the aromatic rings is 87.8 (2)°. In the crystal, inversion dimers occur linked by pairs of N-H⋯S hydrogen bonds.

Related literature

For background to carbodithio­ates, see: Tarafder et al. (2002 ▶).

Experimental

Crystal data

C15H13N3O2S2

M = 331.40

Monoclinic,

a = 5.2175 (10) Å

b = 26.213 (5) Å

c = 11.887 (2) Å

β = 90.67 (3)°

V = 1625.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.30 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.906, T max = 0.967

9486 measured reflections

2788 independent reflections

951 reflections with I > 2σ(I)

R int = 0.097

200 standard reflections every 3 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.106

S = 0.73

2788 reflections

211 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045723/hb5203sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045723/hb5203Isup2.hkl

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

C15H13N3O2S2	F(000) = 688
Mr = 331.40	Dx = 1.354 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 5.2175 (10) Å	θ = 9–12°
b = 26.213 (5) Å	µ = 0.34 mm−1
c = 11.887 (2) Å	T = 293 K
β = 90.67 (3)°	Block, yellow
V = 1625.6 (6) Å3	0.30 × 0.30 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	951 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.097
graphite	θmax = 25.0°, θmin = 1.9°
ω/2θ scans	h = −6→5
Absorption correction: ψ scan (North et al., 1968)	k = −31→29
Tmin = 0.906, Tmax = 0.967	l = −14→14
9486 measured reflections	200 standard reflections every 3 reflections
2788 independent reflections	intensity decay: 1%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 0.73	w = 1/[σ2(Fo2) + (0.0448P)2] where P = (Fo2 + 2Fc2)/3
2788 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 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
C1	1.5564 (10)	0.38939 (18)	1.0058 (4)	0.1065 (16)
H1	1.6613	0.3787	0.9477	0.128*
C2	1.5833 (10)	0.36729 (18)	1.1102 (5)	0.1215 (18)
H2	1.7070	0.3423	1.1222	0.146*
C3	1.4312 (11)	0.38176 (19)	1.1951 (4)	0.0986 (14)
H3	1.4491	0.3668	1.2658	0.118*
C4	1.2549 (11)	0.4177 (2)	1.1770 (4)	0.1203 (18)
H4	1.1474	0.4275	1.2349	0.144*
C5	1.2307 (9)	0.44050 (17)	1.0726 (5)	0.1170 (17)
H5	1.1095	0.4661	1.0616	0.140*
C6	1.3817 (9)	0.42606 (17)	0.9862 (4)	0.0740 (11)
C7	1.3604 (11)	0.4511 (2)	0.8717 (4)	0.0893 (15)
C8	1.0763 (8)	0.45488 (13)	0.6740 (3)	0.0662 (10)
C9	0.5747 (8)	0.38503 (16)	0.5578 (3)	0.0740 (12)
H9	0.5412	0.4063	0.4967	0.089*
C10	0.4214 (8)	0.33846 (15)	0.5727 (3)	0.0648 (10)
C11	0.2307 (8)	0.32751 (16)	0.4958 (3)	0.0716 (11)
H11	0.1940	0.3499	0.4371	0.086*
C12	0.0946 (8)	0.28268 (18)	0.5071 (4)	0.0763 (12)
C13	0.1352 (9)	0.24961 (16)	0.5946 (4)	0.0997 (15)
H13	0.0389	0.2199	0.6014	0.120*
C14	0.3244 (9)	0.26178 (18)	0.6727 (4)	0.1020 (15)
H14	0.3563	0.2399	0.7329	0.122*
C15	0.4658 (8)	0.30577 (16)	0.6623 (3)	0.0838 (12)
H15	0.5917	0.3136	0.7156	0.101*
H1A	0.851 (7)	0.4589 (13)	0.540 (3)	0.100 (15)*
N1	0.8928 (7)	0.43995 (14)	0.6035 (3)	0.0779 (10)
N2	0.7523 (7)	0.39663 (13)	0.6274 (3)	0.0739 (9)
N3	−0.1075 (8)	0.27046 (17)	0.4218 (4)	0.0953 (12)
O1	−0.1536 (6)	0.30218 (13)	0.3506 (3)	0.1166 (11)
O2	−0.2120 (8)	0.22932 (15)	0.4285 (3)	0.1572 (16)
S1	1.1060 (2)	0.41799 (4)	0.79464 (9)	0.0806 (4)
S2	1.2592 (2)	0.50568 (4)	0.64490 (9)	0.0898 (4)
H7A	1.508 (7)	0.4456 (14)	0.827 (3)	0.109 (17)*
H7B	1.308 (8)	0.4842 (16)	0.871 (3)	0.14 (2)*

	U11	U22	U33	U12	U13	U23
C1	0.121 (4)	0.107 (4)	0.092 (4)	0.028 (3)	0.039 (3)	0.019 (3)
C2	0.128 (4)	0.128 (4)	0.109 (4)	0.051 (3)	0.027 (4)	0.034 (4)
C3	0.108 (4)	0.102 (4)	0.085 (4)	0.000 (3)	−0.004 (3)	0.005 (3)
C4	0.135 (5)	0.142 (5)	0.084 (4)	0.029 (4)	0.022 (3)	−0.002 (3)
C5	0.123 (4)	0.132 (4)	0.097 (4)	0.060 (3)	0.015 (3)	0.008 (3)
C6	0.070 (3)	0.076 (3)	0.076 (3)	−0.005 (2)	−0.005 (3)	−0.001 (3)
C7	0.077 (4)	0.109 (5)	0.082 (4)	−0.009 (3)	−0.010 (3)	0.016 (3)
C8	0.063 (3)	0.068 (3)	0.068 (3)	−0.002 (2)	0.001 (2)	0.007 (2)
C9	0.080 (3)	0.078 (3)	0.064 (3)	−0.005 (3)	0.002 (3)	0.005 (2)
C10	0.063 (3)	0.063 (3)	0.068 (3)	−0.006 (2)	0.006 (2)	0.000 (2)
C11	0.068 (3)	0.079 (3)	0.067 (3)	−0.007 (3)	0.003 (3)	0.005 (2)
C12	0.070 (3)	0.089 (4)	0.069 (3)	−0.012 (3)	−0.002 (3)	0.000 (3)
C13	0.103 (4)	0.089 (3)	0.107 (4)	−0.033 (3)	−0.017 (3)	0.027 (3)
C14	0.111 (4)	0.087 (4)	0.108 (4)	−0.020 (3)	−0.015 (3)	0.035 (3)
C15	0.094 (3)	0.078 (3)	0.079 (3)	−0.006 (3)	−0.013 (2)	0.012 (3)
N1	0.080 (3)	0.079 (3)	0.075 (3)	−0.010 (2)	−0.008 (2)	0.015 (2)
N2	0.076 (3)	0.068 (2)	0.077 (2)	−0.005 (2)	0.002 (2)	0.0053 (19)
N3	0.096 (3)	0.097 (4)	0.094 (3)	−0.010 (3)	−0.005 (3)	0.000 (3)
O1	0.114 (3)	0.127 (3)	0.108 (2)	−0.019 (2)	−0.031 (2)	0.016 (2)
O2	0.180 (4)	0.141 (3)	0.150 (3)	−0.082 (3)	−0.045 (3)	0.017 (3)
S1	0.0798 (8)	0.0879 (8)	0.0741 (7)	−0.0113 (6)	0.0010 (6)	0.0101 (6)
S2	0.0950 (9)	0.0826 (8)	0.0917 (8)	−0.0215 (7)	−0.0063 (6)	0.0142 (6)

C1—C6	1.343 (5)	C9—N2	1.272 (4)
C1—C2	1.375 (5)	C9—C10	1.471 (5)
C1—H1	0.9300	C9—H9	0.9300
C2—C3	1.346 (5)	C10—C11	1.373 (4)
C2—H2	0.9300	C10—C15	1.384 (5)
C3—C4	1.332 (5)	C11—C12	1.380 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.381 (5)	C12—C13	1.368 (5)
C4—H4	0.9300	C12—N3	1.489 (5)
C5—C6	1.355 (5)	C13—C14	1.384 (5)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.514 (5)	C14—C15	1.375 (5)
C7—S1	1.823 (5)	C14—H14	0.9300
C7—H7A	0.95 (4)	C15—H15	0.9300
C7—H7B	0.91 (4)	N1—N2	1.383 (4)
C8—N1	1.324 (4)	N1—H1A	0.93 (3)
C8—S2	1.676 (4)	N3—O1	1.208 (4)
C8—S1	1.735 (4)	N3—O2	1.212 (4)
C6—C1—C2	121.3 (4)	N2—C9—H9	119.6
C6—C1—H1	119.3	C10—C9—H9	119.6
C2—C1—H1	119.3	C11—C10—C15	119.7 (4)
C3—C2—C1	120.2 (5)	C11—C10—C9	118.9 (4)
C3—C2—H2	119.9	C15—C10—C9	121.3 (4)
C1—C2—H2	119.9	C10—C11—C12	118.9 (4)
C4—C3—C2	119.3 (5)	C10—C11—H11	120.6
C4—C3—H3	120.3	C12—C11—H11	120.6
C2—C3—H3	120.3	C13—C12—C11	122.5 (4)
C3—C4—C5	120.5 (5)	C13—C12—N3	118.9 (4)
C3—C4—H4	119.8	C11—C12—N3	118.5 (4)
C5—C4—H4	119.8	C12—C13—C14	117.8 (4)
C6—C5—C4	120.8 (4)	C12—C13—H13	121.1
C6—C5—H5	119.6	C14—C13—H13	121.1
C4—C5—H5	119.6	C15—C14—C13	120.8 (4)
C1—C6—C5	117.9 (4)	C15—C14—H14	119.6
C1—C6—C7	120.6 (5)	C13—C14—H14	119.6
C5—C6—C7	121.6 (5)	C14—C15—C10	120.2 (4)
C6—C7—S1	106.9 (3)	C14—C15—H15	119.9
C6—C7—H7A	113 (2)	C10—C15—H15	119.9
S1—C7—H7A	104 (2)	C8—N1—N2	119.6 (4)
C6—C7—H7B	116 (3)	C8—N1—H1A	121 (2)
S1—C7—H7B	104 (3)	N2—N1—H1A	119 (2)
H7A—C7—H7B	113 (4)	C9—N2—N1	116.5 (4)
N1—C8—S2	120.9 (3)	O1—N3—O2	124.9 (5)
N1—C8—S1	114.5 (3)	O1—N3—C12	117.6 (4)
S2—C8—S1	124.6 (3)	O2—N3—C12	117.5 (5)
N2—C9—C10	120.9 (4)	C8—S1—C7	102.0 (2)
C6—C1—C2—C3	0.8 (8)	N3—C12—C13—C14	179.9 (4)
C1—C2—C3—C4	−0.1 (8)	C12—C13—C14—C15	0.1 (7)
C2—C3—C4—C5	−1.0 (8)	C13—C14—C15—C10	−0.4 (6)
C3—C4—C5—C6	1.4 (8)	C11—C10—C15—C14	1.7 (6)
C2—C1—C6—C5	−0.4 (7)	C9—C10—C15—C14	−178.3 (3)
C2—C1—C6—C7	178.1 (4)	S2—C8—N1—N2	177.2 (2)
C4—C5—C6—C1	−0.7 (7)	S1—C8—N1—N2	−2.9 (4)
C4—C5—C6—C7	−179.2 (4)	C10—C9—N2—N1	177.3 (3)
C1—C6—C7—S1	96.1 (5)	C8—N1—N2—C9	178.3 (3)
C5—C6—C7—S1	−85.4 (5)	C13—C12—N3—O1	174.2 (4)
N2—C9—C10—C11	179.7 (3)	C11—C12—N3—O1	−4.7 (6)
N2—C9—C10—C15	−0.3 (5)	C13—C12—N3—O2	−6.3 (6)
C15—C10—C11—C12	−2.8 (5)	C11—C12—N3—O2	174.8 (4)
C9—C10—C11—C12	177.2 (3)	N1—C8—S1—C7	−177.5 (3)
C10—C11—C12—C13	2.6 (6)	S2—C8—S1—C7	2.4 (3)
C10—C11—C12—N3	−178.5 (3)	C6—C7—S1—C8	173.1 (4)
C11—C12—C13—C14	−1.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S2i	0.93 (3)	2.45 (4)	3.365 (4)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S2i	0.93 (3)	2.45 (4)	3.365 (4)	170 (3)

Symmetry code: (i) .