Benzyl N′-(1H-indol-3-ylmethyl­idene)­hydrazinecarbodithio­ate

Khaledi, H.; Mohd Ali, H.; Ng, S.W.

doi:10.1107/S160053680803198X

organic compounds

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Volume 64| Part 11| November 2008| Page o2107

doi:10.1107/S160053680803198X

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Benzyl N′-(1H-indol-3-ylmethylidene)hydrazinecarbodithioate

Hamid Khaledi,^a Hapipah Mohd Ali ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 September 2008; accepted 5 October 2008; online 11 October 2008)

The C₁₀H₈N₃S₂ portion of the title molecule, C₁₇H₁₅N₃S₃, 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 methylene 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_r = 325.44
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.118
S = 1.01
3383 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −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 ).

Supporting information

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

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

checkCIF report

Comment top

The structure of (I), Fig. 1, shows bond distances for N1—N2 and N2—C9 of 1.382 (3) and 1.287 (3) Å, respectively, confirming the assignment shown in the Scheme. The molecule is bent about the methylene-C7 atom so that the residues on either side are approximately orthogonal. The amino groups do not form any hydrogen bonds.

Related literature top

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 top

Indole-3-carbaldehyde (0.37 g, 2.5 mmol) and S-benzyl dithiocarbazate (0.50 g, 2.5 mmol) were heated in methanol (40 ml) for 3 h. The solution was set aside for the formation of yellow crystals.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₇H₁₅N₂S₃ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Benzyl N'-(1H-indol-3-ylmethylidene)hydrazinecarbodithioate top

Crystal data top

C₁₇H₁₅N₃S₂	F(000) = 680
M_r = 325.44	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0391P)² + 1.1115P] where P = (F_o² + 2F_c²)/3
3383 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₇H₁₅N₃S₂	V = 1541.8 (1) Å³
M_r = 325.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.4936 (7) Å	µ = 0.34 mm⁻¹
b = 9.8114 (4) Å	T = 100 K
c = 10.2531 (4) Å	0.25 × 0.10 × 0.03 mm
β = 98.432 (3)°

Data collection top

Bruker SMART APEX diffractometer	3383 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2323 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.990	R_int = 0.058
8531 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.01	Δρ_max = 0.48 e Å⁻³
3383 reflections	Δρ_min = −0.33 e Å⁻³
199 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅N₃S₂
M_r	325.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	15.4936 (7), 9.8114 (4), 10.2531 (4)
β (°)	98.432 (3)
V (Å³)	1541.8 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.25 × 0.10 × 0.03

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.919, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	8531, 3383, 2323
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.118, 1.01
No. of reflections	3383
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Acknowledgements

The authors thank the University of Malaya for funding this study (Science Fund Grants 12-02-03-2031 and 12-02-03-2051).

References

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