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

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

doi:10.1107/S160053680803198X

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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680803198X/tk2309sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680803198X/tk2309Isup2.hkl Contains datablock I

CCDC reference: 709349

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R factor = 0.049
wR factor = 0.118
Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
            Value of measurement temperature given =   100.000
            Value of melting point given =     0.000
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3     ...          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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).

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

Supporting information

Key indicators

checkCIF/PLATON results

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