Benzyl N'-(1H-indol-3-ylmethyl-idene)-hydrazinecarbodithio-ate.

The C(10)H(8)N(3)S(2) portion of the title mol-ecule, C(17)H(15)N(3)S(3), is nearly planar (r.m.s. deviation 0.05 Å); this unit and the phenyl ring subtend an angle of 114.5 (2)° at the methyl-ene C atom.

Related literature

For other Schiff bases derived by condensing S-benzyl hydrazinecarbodithio­ate with either aromatic aldehydes or ketones, see: Ali et al. (2004 ▶); Chan et al. (2003 ▶); Fun et al. (1995 ▶); How et al. (2007a ▶,b ▶,c ▶); Khoo et al. (2005 ▶); Qiu & Luo (2007 ▶); Roy et al. (2007 ▶); Tarafder et al. (2002 ▶); Xu et al. (1991 ▶); Zhang et al. (2004 ▶).

Experimental

Crystal data

C17H15N3S2

M = 325.44

Monoclinic,

a = 15.4936 (7) Å

b = 9.8114 (4) Å

c = 10.2531 (4) Å

β = 98.432 (3)°

V = 1541.8 (1) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 100 (2) K

0.25 × 0.10 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.919, T max = 0.990

8531 measured reflections

3383 independent reflections

2323 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.118

S = 1.01

3383 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803198X/tk2309sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803198X/tk2309Isup2.hkl

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

C17H15N3S2	F(000) = 680
Mr = 325.44	Dx = 1.402 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1305 reflections
a = 15.4936 (7) Å	θ = 2.5–23.2°
b = 9.8114 (4) Å	µ = 0.34 mm−1
c = 10.2531 (4) Å	T = 100 K
β = 98.432 (3)°	Prism, light yellow
V = 1541.8 (1) Å3	0.25 × 0.10 × 0.03 mm
Z = 4

Bruker SMART APEX diffractometer	3383 independent reflections
Radiation source: fine-focus sealed tube	2323 reflections with I > 2σ(I)
graphite	Rint = 0.058
ω scans	θmax = 27°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.919, Tmax = 0.990	k = −12→12
8531 measured reflections	l = −13→8

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0391P)2 + 1.1115P] where P = (Fo2 + 2Fc2)/3
3383 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.75015 (5)	0.74458 (7)	0.47255 (7)	0.02090 (18)
S2	0.87340 (5)	0.53986 (7)	0.36891 (7)	0.02198 (19)
N1	0.70350 (15)	0.5227 (2)	0.3457 (2)	0.0217 (5)
H1	0.7086	0.4440	0.3063	0.026*
N2	0.62145 (15)	0.5704 (2)	0.3596 (2)	0.0212 (5)
N3	0.32371 (16)	0.5105 (2)	0.2983 (2)	0.0253 (6)
H3	0.2706	0.4795	0.2732	0.030*
C1	0.87962 (17)	0.9360 (3)	0.4432 (3)	0.0188 (6)
C2	0.89308 (18)	0.9185 (3)	0.3115 (3)	0.0216 (6)
H2	0.8855	0.8312	0.2714	0.026*
C3	0.91737 (18)	1.0283 (3)	0.2403 (3)	0.0242 (7)
H3a	0.9272	1.0156	0.1518	0.029*
C4	0.92738 (18)	1.1564 (3)	0.2970 (3)	0.0259 (7)
H4	0.9436	1.2316	0.2475	0.031*
C5	0.91353 (19)	1.1742 (3)	0.4261 (3)	0.0245 (7)
H5	0.9202	1.2619	0.4654	0.029*
C6	0.89010 (18)	1.0647 (3)	0.4983 (3)	0.0212 (6)
H6	0.8811	1.0780	0.5871	0.025*
C7	0.85739 (18)	0.8174 (3)	0.5249 (3)	0.0210 (6)
H7A	0.8609	0.8475	0.6176	0.025*
H7B	0.9018	0.7453	0.5220	0.025*
C8	0.77530 (18)	0.5938 (3)	0.3909 (3)	0.0191 (6)
C9	0.55868 (18)	0.4859 (3)	0.3251 (3)	0.0209 (6)
H9	0.5717	0.3976	0.2953	0.025*
C10	0.46972 (19)	0.5221 (3)	0.3305 (3)	0.0204 (6)
C11	0.39833 (19)	0.4445 (3)	0.2826 (3)	0.0230 (6)
H11	0.4009	0.3569	0.2438	0.028*
C12	0.43633 (18)	0.6451 (3)	0.3827 (3)	0.0197 (6)
C13	0.47407 (19)	0.7591 (3)	0.4513 (3)	0.0217 (6)
H13	0.5357	0.7694	0.4680	0.026*
C14	0.42007 (19)	0.8557 (3)	0.4939 (3)	0.0255 (7)
H14	0.4452	0.9328	0.5412	0.031*
C15	0.3294 (2)	0.8434 (3)	0.4694 (3)	0.0285 (7)
H15	0.2941	0.9122	0.4997	0.034*
C16	0.2901 (2)	0.7323 (3)	0.4016 (3)	0.0284 (7)
H16	0.2284	0.7238	0.3842	0.034*
C17	0.34423 (19)	0.6341 (3)	0.3602 (3)	0.0222 (6)

	U11	U22	U33	U12	U13	U23
S1	0.0225 (4)	0.0184 (3)	0.0229 (4)	−0.0009 (3)	0.0070 (3)	−0.0025 (3)
S2	0.0234 (4)	0.0212 (4)	0.0226 (4)	0.0034 (3)	0.0075 (3)	0.0014 (3)
N1	0.0231 (13)	0.0194 (12)	0.0234 (14)	−0.0005 (10)	0.0060 (11)	−0.0047 (10)
N2	0.0197 (12)	0.0236 (13)	0.0211 (14)	−0.0023 (10)	0.0062 (10)	0.0016 (11)
N3	0.0220 (13)	0.0285 (14)	0.0249 (14)	−0.0048 (11)	0.0022 (11)	0.0006 (11)
C1	0.0166 (14)	0.0203 (14)	0.0195 (16)	−0.0007 (11)	0.0027 (12)	0.0006 (12)
C2	0.0223 (15)	0.0239 (15)	0.0181 (16)	−0.0013 (12)	0.0012 (12)	−0.0037 (12)
C3	0.0235 (15)	0.0337 (17)	0.0158 (15)	0.0008 (13)	0.0038 (12)	0.0034 (13)
C4	0.0236 (15)	0.0250 (15)	0.0295 (19)	−0.0006 (13)	0.0045 (13)	0.0106 (14)
C5	0.0262 (16)	0.0198 (15)	0.0277 (18)	0.0005 (12)	0.0041 (13)	−0.0016 (13)
C6	0.0228 (15)	0.0218 (15)	0.0196 (16)	0.0036 (12)	0.0050 (12)	−0.0002 (12)
C7	0.0227 (15)	0.0209 (15)	0.0196 (16)	−0.0006 (12)	0.0032 (12)	−0.0010 (12)
C8	0.0265 (15)	0.0170 (14)	0.0149 (15)	0.0008 (11)	0.0064 (12)	0.0024 (11)
C9	0.0277 (16)	0.0217 (15)	0.0142 (15)	−0.0022 (12)	0.0058 (12)	−0.0003 (12)
C10	0.0268 (15)	0.0201 (14)	0.0140 (15)	−0.0048 (12)	0.0020 (12)	0.0024 (12)
C11	0.0297 (16)	0.0217 (15)	0.0180 (16)	−0.0046 (13)	0.0054 (13)	0.0009 (13)
C12	0.0233 (15)	0.0220 (15)	0.0143 (15)	−0.0039 (12)	0.0044 (12)	0.0040 (12)
C13	0.0227 (15)	0.0248 (15)	0.0177 (16)	−0.0043 (12)	0.0037 (12)	0.0041 (13)
C14	0.0315 (17)	0.0253 (16)	0.0205 (17)	−0.0039 (13)	0.0063 (13)	−0.0028 (13)
C15	0.0291 (17)	0.0296 (17)	0.0277 (18)	0.0022 (14)	0.0077 (14)	−0.0038 (14)
C16	0.0231 (16)	0.0340 (18)	0.0281 (18)	−0.0034 (13)	0.0040 (13)	0.0005 (15)
C17	0.0272 (16)	0.0228 (15)	0.0163 (15)	−0.0057 (12)	0.0025 (12)	0.0034 (12)

S1—C8	1.771 (3)	C5—H5	0.9500
S1—C7	1.816 (3)	C6—H6	0.9500
S2—C8	1.656 (3)	C7—H7A	0.9900
N1—C8	1.337 (4)	C7—H7B	0.9900
N1—N2	1.382 (3)	C9—C10	1.432 (4)
N1—H1	0.8800	C9—H9	0.9500
N2—C9	1.287 (3)	C10—C11	1.373 (4)
N3—C11	1.355 (4)	C10—C12	1.446 (4)
N3—C17	1.384 (4)	C11—H11	0.9500
N3—H3	0.8800	C12—C13	1.402 (4)
C1—C6	1.383 (4)	C12—C17	1.416 (4)
C1—C2	1.407 (4)	C13—C14	1.377 (4)
C1—C7	1.503 (4)	C13—H13	0.9500
C2—C3	1.384 (4)	C14—C15	1.395 (4)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.384 (4)	C15—C16	1.385 (4)
C3—H3a	0.9500	C15—H15	0.9500
C4—C5	1.384 (4)	C16—C17	1.384 (4)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.383 (4)
C8—S1—C7	102.30 (13)	H7A—C7—H7B	107.6
C8—N1—N2	121.2 (2)	N1—C8—S2	121.3 (2)
C8—N1—H1	119.4	N1—C8—S1	111.7 (2)
N2—N1—H1	119.4	S2—C8—S1	126.97 (17)
C9—N2—N1	115.0 (2)	N2—C9—C10	121.5 (3)
C11—N3—C17	109.3 (2)	N2—C9—H9	119.3
C11—N3—H3	125.4	C10—C9—H9	119.3
C17—N3—H3	125.4	C11—C10—C9	125.3 (3)
C6—C1—C2	118.6 (3)	C11—C10—C12	106.4 (3)
C6—C1—C7	120.1 (3)	C9—C10—C12	128.3 (3)
C2—C1—C7	121.2 (3)	N3—C11—C10	110.4 (3)
C3—C2—C1	120.1 (3)	N3—C11—H11	124.8
C3—C2—H2	119.9	C10—C11—H11	124.8
C1—C2—H2	119.9	C13—C12—C17	118.6 (3)
C4—C3—C2	120.5 (3)	C13—C12—C10	134.9 (3)
C4—C3—H3a	119.8	C17—C12—C10	106.4 (2)
C2—C3—H3a	119.8	C14—C13—C12	118.7 (3)
C3—C4—C5	119.5 (3)	C14—C13—H13	120.7
C3—C4—H4	120.2	C12—C13—H13	120.7
C5—C4—H4	120.2	C13—C14—C15	121.7 (3)
C4—C5—C6	120.3 (3)	C13—C14—H14	119.2
C4—C5—H5	119.9	C15—C14—H14	119.2
C6—C5—H5	119.9	C16—C15—C14	121.0 (3)
C5—C6—C1	121.0 (3)	C16—C15—H15	119.5
C5—C6—H6	119.5	C14—C15—H15	119.5
C1—C6—H6	119.5	C17—C16—C15	117.4 (3)
C1—C7—S1	114.5 (2)	C17—C16—H16	121.3
C1—C7—H7A	108.6	C15—C16—H16	121.3
S1—C7—H7A	108.6	C16—C17—N3	129.9 (3)
C1—C7—H7B	108.6	C16—C17—C12	122.6 (3)
S1—C7—H7B	108.6	N3—C17—C12	107.4 (2)
C8—N1—N2—C9	−172.7 (3)	C9—C10—C11—N3	−177.4 (3)
C6—C1—C2—C3	0.8 (4)	C12—C10—C11—N3	1.3 (3)
C7—C1—C2—C3	−177.1 (3)	C11—C10—C12—C13	175.2 (3)
C1—C2—C3—C4	−1.0 (4)	C9—C10—C12—C13	−6.2 (5)
C2—C3—C4—C5	0.5 (4)	C11—C10—C12—C17	−1.0 (3)
C3—C4—C5—C6	0.2 (4)	C9—C10—C12—C17	177.7 (3)
C4—C5—C6—C1	−0.3 (4)	C17—C12—C13—C14	0.0 (4)
C2—C1—C6—C5	−0.2 (4)	C10—C12—C13—C14	−175.8 (3)
C7—C1—C6—C5	177.7 (3)	C12—C13—C14—C15	−0.6 (4)
C6—C1—C7—S1	113.9 (3)	C13—C14—C15—C16	0.4 (5)
C2—C1—C7—S1	−68.2 (3)	C14—C15—C16—C17	0.4 (5)
C8—S1—C7—C1	103.7 (2)	C15—C16—C17—N3	175.7 (3)
N2—N1—C8—S2	−177.5 (2)	C15—C16—C17—C12	−1.1 (4)
N2—N1—C8—S1	2.6 (3)	C11—N3—C17—C16	−176.7 (3)
C7—S1—C8—N1	179.0 (2)	C11—N3—C17—C12	0.4 (3)
C7—S1—C8—S2	−0.9 (2)	C13—C12—C17—C16	0.9 (4)
N1—N2—C9—C10	−178.3 (2)	C10—C12—C17—C16	177.8 (3)
N2—C9—C10—C11	172.6 (3)	C13—C12—C17—N3	−176.6 (2)
N2—C9—C10—C12	−5.8 (5)	C10—C12—C17—N3	0.3 (3)
C17—N3—C11—C10	−1.1 (3)