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

The N'-(1-methyl-1H-indol-3-ylmethyl-idene)hydrazine-carbo-dithio-ate portion of the title mol-ecule, C(18)H(17)N(3)S(2), is nearly planar; this unit and the phenyl ring subtend an angle of 112.9 (2)° at the methyl-ene C atom.

Related literature

For the structure of S-benzyl N-1-(1H-indol-3-ylmethyl­idenehydrazinecarbodithio­ate, see: Khaledi et al. (2008 ▶).

Experimental

Crystal data

C18H17N3S2

M = 339.47

Monoclinic,

a = 10.6111 (4) Å

b = 6.1134 (2) Å

c = 13.4961 (4) Å

β = 111.934 (2)°

V = 812.12 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 100 (2) K

0.30 × 0.10 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.908, T max = 0.993

5513 measured reflections

3277 independent reflections

2802 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.087

S = 1.03

3277 reflections

213 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 1261 Friedel pairs

Flack parameter: 0.01 (8)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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/S1600536808039330/tk2334sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039330/tk2334Isup2.hkl

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

C18H17N3S2	F000 = 356
Mr = 339.47	Dx = 1.388 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1721 reflections
a = 10.6111 (4) Å	θ = 3.1–27.1º
b = 6.1134 (2) Å	µ = 0.33 mm−1
c = 13.4961 (4) Å	T = 100 (2) K
β = 111.934 (2)º	Plate, yellow
V = 812.12 (5) Å3	0.30 × 0.10 × 0.02 mm
Z = 2

Bruker SMART APEX diffractometer	3277 independent reflections
Radiation source: fine-focus sealed tube	2802 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
T = 100(2) K	θmax = 27.5º
ω scans	θmin = 1.6º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.908, Tmax = 0.993	k = −6→7
5513 measured reflections	l = −17→17

Refinement on F2	Hydrogen site location: constr
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0366P)2 + 0.212P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.28 e Å−3
3277 reflections	Δρmin = −0.28 e Å−3
213 parameters	Extinction correction: none
2 restraints	Absolute structure: Flack (1983), 1261 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (8)
Secondary atom site location: difference Fourier map

	x	y	z	Uiso*/Ueq
S1	0.33191 (7)	0.50000 (12)	0.67816 (5)	0.01960 (16)
S2	0.48123 (7)	0.86601 (13)	0.61270 (5)	0.02642 (18)
N1	0.2902 (2)	0.7662 (4)	1.16590 (16)	0.0202 (5)
N2	0.3791 (2)	0.7502 (4)	0.85695 (16)	0.0181 (5)
N3	0.4323 (2)	0.8477 (4)	0.78860 (16)	0.0183 (5)
H3	0.480 (3)	0.967 (3)	0.796 (2)	0.035 (9)*
C1	0.2337 (3)	0.5789 (5)	1.1079 (2)	0.0178 (6)
C2	0.1584 (3)	0.4147 (5)	1.1303 (2)	0.0215 (6)
H2	0.1422	0.4143	1.1950	0.026*
C3	0.1075 (3)	0.2515 (5)	1.0548 (2)	0.0236 (6)
H3A	0.0531	0.1389	1.0668	0.028*
C4	0.1347 (3)	0.2496 (5)	0.9610 (2)	0.0215 (6)
H4	0.0983	0.1354	0.9106	0.026*
C5	0.2133 (3)	0.4101 (4)	0.9399 (2)	0.0193 (6)
H5	0.2326	0.4051	0.8767	0.023*
C6	0.2637 (3)	0.5795 (4)	1.01374 (19)	0.0166 (6)
C7	0.2743 (3)	0.8324 (5)	1.2645 (2)	0.0261 (7)
H7A	0.3162	0.9761	1.2867	0.039*
H7B	0.3186	0.7249	1.3206	0.039*
H7C	0.1774	0.8405	1.2524	0.039*
C8	0.3524 (3)	0.8815 (5)	1.11224 (19)	0.0201 (6)
H8	0.3981	1.0166	1.1357	0.024*
C9	0.3409 (3)	0.7767 (4)	1.01840 (19)	0.0168 (6)
C10	0.3932 (2)	0.8586 (5)	0.94249 (18)	0.0166 (5)
H10	0.4392	0.9952	0.9551	0.020*
C11	0.4177 (3)	0.7519 (5)	0.6953 (2)	0.0197 (6)
C12	0.3161 (3)	0.4207 (5)	0.54473 (19)	0.0229 (6)
H12A	0.3840	0.5019	0.5251	0.028*
H12B	0.3366	0.2627	0.5445	0.028*
C13	0.1765 (3)	0.4642 (5)	0.46213 (19)	0.0192 (6)
C14	0.1145 (3)	0.6657 (5)	0.4536 (2)	0.0220 (6)
H14	0.1606	0.7800	0.5010	0.026*
C15	−0.0137 (3)	0.7043 (5)	0.3773 (2)	0.0258 (7)
H15	−0.0550	0.8438	0.3726	0.031*
C16	−0.0816 (3)	0.5379 (6)	0.3078 (2)	0.0295 (8)
H16	−0.1693	0.5638	0.2552	0.035*
C17	−0.0220 (3)	0.3353 (5)	0.3150 (2)	0.0280 (7)
H17	−0.0686	0.2212	0.2677	0.034*
C18	0.1073 (3)	0.2984 (5)	0.3919 (2)	0.0240 (7)
H18	0.1486	0.1589	0.3966	0.029*

	U11	U22	U33	U12	U13	U23
S1	0.0229 (3)	0.0209 (4)	0.0149 (3)	−0.0023 (3)	0.0070 (2)	0.0006 (3)
S2	0.0317 (4)	0.0286 (4)	0.0252 (3)	−0.0013 (4)	0.0179 (3)	0.0058 (3)
N1	0.0225 (12)	0.0243 (13)	0.0158 (10)	0.0007 (10)	0.0094 (9)	−0.0026 (9)
N2	0.0191 (11)	0.0187 (13)	0.0176 (10)	−0.0022 (10)	0.0082 (9)	0.0036 (9)
N3	0.0232 (12)	0.0166 (13)	0.0178 (10)	−0.0018 (10)	0.0109 (9)	0.0023 (10)
C1	0.0179 (14)	0.0190 (15)	0.0159 (12)	0.0050 (12)	0.0056 (11)	0.0017 (11)
C2	0.0210 (14)	0.0248 (17)	0.0208 (13)	0.0049 (12)	0.0103 (11)	0.0051 (11)
C3	0.0217 (14)	0.0195 (16)	0.0298 (14)	−0.0007 (13)	0.0097 (12)	0.0052 (12)
C4	0.0225 (14)	0.0195 (15)	0.0208 (13)	−0.0007 (12)	0.0062 (11)	−0.0012 (12)
C5	0.0192 (13)	0.0213 (16)	0.0178 (12)	0.0031 (12)	0.0072 (11)	0.0025 (11)
C6	0.0145 (13)	0.0187 (15)	0.0169 (12)	0.0041 (11)	0.0063 (10)	0.0031 (11)
C7	0.0369 (17)	0.0297 (18)	0.0160 (12)	0.0016 (14)	0.0148 (12)	−0.0056 (12)
C8	0.0173 (13)	0.0194 (15)	0.0216 (12)	0.0007 (13)	0.0049 (10)	−0.0003 (12)
C9	0.0156 (13)	0.0182 (15)	0.0157 (12)	0.0003 (11)	0.0048 (10)	0.0016 (11)
C10	0.0180 (13)	0.0136 (13)	0.0168 (11)	−0.0014 (12)	0.0049 (10)	−0.0002 (11)
C11	0.0176 (13)	0.0225 (16)	0.0185 (12)	0.0038 (12)	0.0061 (11)	0.0040 (11)
C12	0.0298 (15)	0.0225 (16)	0.0182 (12)	0.0035 (12)	0.0109 (12)	−0.0016 (11)
C13	0.0230 (13)	0.0242 (17)	0.0130 (11)	−0.0008 (12)	0.0099 (10)	0.0005 (11)
C14	0.0230 (15)	0.0266 (17)	0.0157 (12)	−0.0016 (12)	0.0064 (11)	−0.0021 (11)
C15	0.0281 (16)	0.0256 (17)	0.0254 (14)	0.0045 (13)	0.0122 (12)	0.0060 (13)
C16	0.0244 (15)	0.044 (2)	0.0176 (12)	−0.0029 (14)	0.0055 (11)	0.0064 (13)
C17	0.0353 (17)	0.0324 (19)	0.0169 (12)	−0.0157 (15)	0.0105 (12)	−0.0049 (13)
C18	0.0366 (17)	0.0196 (16)	0.0202 (13)	−0.0043 (13)	0.0159 (13)	−0.0011 (11)

S1—C11	1.759 (3)	C7—H7A	0.9800
S1—C12	1.811 (3)	C7—H7B	0.9800
S2—C11	1.657 (3)	C7—H7C	0.9800
N1—C8	1.347 (3)	C8—C9	1.383 (4)
N1—C1	1.390 (4)	C8—H8	0.9500
N1—C7	1.460 (3)	C9—C10	1.426 (4)
N2—C10	1.290 (3)	C10—H10	0.9500
N2—N3	1.384 (3)	C12—C13	1.508 (4)
N3—C11	1.345 (3)	C12—H12A	0.9900
N3—H3	0.875 (10)	C12—H12B	0.9900
C1—C2	1.386 (4)	C13—C14	1.381 (4)
C1—C6	1.420 (4)	C13—C18	1.394 (4)
C2—C3	1.384 (4)	C14—C15	1.386 (4)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.400 (4)	C15—C16	1.389 (4)
C3—H3A	0.9500	C15—H15	0.9500
C4—C5	1.385 (4)	C16—C17	1.378 (5)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.398 (4)	C17—C18	1.395 (4)
C5—H5	0.9500	C17—H17	0.9500
C6—C9	1.445 (4)	C18—H18	0.9500
C11—S1—C12	102.48 (13)	C9—C8—H8	124.6
C8—N1—C1	108.8 (2)	C8—C9—C10	124.8 (3)
C8—N1—C7	126.3 (3)	C8—C9—C6	106.3 (2)
C1—N1—C7	124.7 (2)	C10—C9—C6	128.9 (2)
C10—N2—N3	115.8 (2)	N2—C10—C9	121.1 (3)
C11—N3—N2	120.3 (2)	N2—C10—H10	119.5
C11—N3—H3	109 (2)	C9—C10—H10	119.5
N2—N3—H3	131 (2)	N3—C11—S2	120.9 (2)
C2—C1—N1	129.5 (2)	N3—C11—S1	112.2 (2)
C2—C1—C6	122.6 (3)	S2—C11—S1	126.94 (17)
N1—C1—C6	108.0 (2)	C13—C12—S1	112.87 (19)
C3—C2—C1	117.4 (2)	C13—C12—H12A	109.0
C3—C2—H2	121.3	S1—C12—H12A	109.0
C1—C2—H2	121.3	C13—C12—H12B	109.0
C2—C3—C4	121.1 (3)	S1—C12—H12B	109.0
C2—C3—H3A	119.4	H12A—C12—H12B	107.8
C4—C3—H3A	119.4	C14—C13—C18	118.6 (2)
C5—C4—C3	121.6 (3)	C14—C13—C12	121.6 (2)
C5—C4—H4	119.2	C18—C13—C12	119.8 (3)
C3—C4—H4	119.2	C13—C14—C15	121.2 (3)
C4—C5—C6	118.6 (2)	C13—C14—H14	119.4
C4—C5—H5	120.7	C15—C14—H14	119.4
C6—C5—H5	120.7	C14—C15—C16	119.7 (3)
C5—C6—C1	118.8 (2)	C14—C15—H15	120.2
C5—C6—C9	135.2 (2)	C16—C15—H15	120.2
C1—C6—C9	106.0 (2)	C17—C16—C15	120.2 (3)
N1—C7—H7A	109.5	C17—C16—H16	119.9
N1—C7—H7B	109.5	C15—C16—H16	119.9
H7A—C7—H7B	109.5	C16—C17—C18	119.7 (3)
N1—C7—H7C	109.5	C16—C17—H17	120.2
H7A—C7—H7C	109.5	C18—C17—H17	120.2
H7B—C7—H7C	109.5	C13—C18—C17	120.7 (3)
N1—C8—C9	110.9 (3)	C13—C18—H18	119.7
N1—C8—H8	124.6	C17—C18—H18	119.7
C10—N2—N3—C11	−177.2 (2)	C1—C6—C9—C8	−0.2 (3)
C8—N1—C1—C2	−178.6 (3)	C5—C6—C9—C10	−1.0 (5)
C7—N1—C1—C2	−3.0 (4)	C1—C6—C9—C10	−178.3 (3)
C8—N1—C1—C6	0.3 (3)	N3—N2—C10—C9	179.1 (2)
C7—N1—C1—C6	175.9 (2)	C8—C9—C10—N2	179.5 (3)
N1—C1—C2—C3	176.3 (3)	C6—C9—C10—N2	−2.7 (4)
C6—C1—C2—C3	−2.4 (4)	N2—N3—C11—S2	−179.82 (19)
C1—C2—C3—C4	1.8 (4)	N2—N3—C11—S1	−1.8 (3)
C2—C3—C4—C5	0.0 (4)	C12—S1—C11—N3	175.97 (19)
C3—C4—C5—C6	−1.3 (4)	C12—S1—C11—S2	−6.1 (2)
C4—C5—C6—C1	0.8 (4)	C11—S1—C12—C13	−101.3 (2)
C4—C5—C6—C9	−176.2 (3)	S1—C12—C13—C14	50.8 (3)
C2—C1—C6—C5	1.1 (4)	S1—C12—C13—C18	−129.3 (2)
N1—C1—C6—C5	−177.9 (2)	C18—C13—C14—C15	0.0 (4)
C2—C1—C6—C9	178.9 (2)	C12—C13—C14—C15	179.9 (2)
N1—C1—C6—C9	−0.1 (3)	C13—C14—C15—C16	−0.1 (4)
C1—N1—C8—C9	−0.4 (3)	C14—C15—C16—C17	0.3 (4)
C7—N1—C8—C9	−175.9 (3)	C15—C16—C17—C18	−0.4 (4)
N1—C8—C9—C10	178.6 (2)	C14—C13—C18—C17	−0.2 (4)
N1—C8—C9—C6	0.4 (3)	C12—C13—C18—C17	180.0 (2)
C5—C6—C9—C8	177.1 (3)	C16—C17—C18—C13	0.4 (4)