Benzyl N′-(1-methyl-1H-indol-2-ylmethyl­ene)hydrazinecarbodithio­ate

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

doi:10.1107/S1600536808038579

organic compounds

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Volume 64| Part 12| December 2008| Page o2430

doi:10.1107/S1600536808038579

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Benzyl N′-(1-methyl-1H-indol-2-ylmethylene)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 15 November 2008; accepted 19 November 2008; online 26 November 2008)

In the title compound, C₁₈H₁₇N₃S₂, the dihedral angle between the planes of the aromatic ring systems is 83.63 (16)°. In the crystal structure, inversion dimers occur, linked by pairs of N—H⋯S hydrogen bonds.

Related literature

For the crystal structures of the benzyl esters of hydrazinecarbodithioic acids, see: Ali et al. (2004 ); Chan et al. (2003 ); Fun et al. (1995 ); How et al. (2007 ); Khoo et al. (2005 ); Qiu & Luo (2007 ); Roy et al. (2007 ); Tarafder et al. (2002 ); Xu et al. (1991 , 2002 ); Zhang et al. (2004 ).

Experimental

Crystal data

C₁₈H₁₇N₃S₂
M_r = 339.47
Triclinic, $[P \overline 1]$
a = 5.1203 (1) Å
b = 11.9377 (3) Å
c = 14.1936 (4) Å
α = 108.203 (2)°
β = 90.230 (2)°
γ = 96.191 (2)°
V = 818.70 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 100 (2) K
0.40 × 0.08 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.880, T_max = 0.987
7605 measured reflections
3732 independent reflections
2653 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.225
S = 1.13
3732 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 1.56 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2ⁱ	0.88	2.49	3.336 (3)	161
Symmetry code: (i) -x+1, -y+1, -z+1.

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: pubCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038579/hb2848sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038579/hb2848Isup2.hkl

checkCIF report

Comment top

For related structures, see: Ali et al. (2004); Chan et al. (2003); Fun et al. (1995); How et al. (2007); Khoo et al. (2005); Qiu & Luo (2007); Roy et al. (2007); Tarafder et al. (2002); Xu et al. (1991, 2002); Zhang et al. (2004).

Related literature top

For the crystal structures of the benzyl esters of hydrazinecarbodithioic acids, see: Ali et al. (2004); Chan et al. (2003); Fun et al. (1995); How et al. (2007); Khoo et al. (2005); Qiu & Luo (2007); Roy et al. (2007); Tarafder et al. (2002); Xu et al. (1991, 2002); Zhang et al. (2004).

Experimental top

1-Methylindole-2-carbaldehyde (0.40 g, 2.5 mmol) and S-benzyldithiocarbazate (0.50 g, 2.5 mmol) were heated in ethanol (40 ml) for 3 h. The solid that separated on cooling the solution was collected and recrystallized from ethanol and washed with cold ethanol and dried. Orange prisms of (I) were grown by slow evaporation of ethanol solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (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: pubCIF (Westrip, 2008).

Figures top

Fig. 1. The molecular structue of (I) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Benzyl N'-(1-methyl-1H-indol-2-ylmethylene)hydrazinecarbodithioate top

Crystal data top

C₁₈H₁₇N₃S₂	Z = 2
M_r = 339.47	F(000) = 356
Triclinic, P1	D_x = 1.377 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.1203 (1) Å	Cell parameters from 2060 reflections
b = 11.9377 (3) Å	θ = 2.6–28.1°
c = 14.1936 (4) Å	µ = 0.33 mm⁻¹
α = 108.203 (2)°	T = 100 K
β = 90.230 (2)°	Prism, orange
γ = 96.191 (2)°	0.40 × 0.08 × 0.04 mm
V = 818.70 (3) Å³

Data collection top

Bruker SMART APEX diffractometer	3732 independent reflections
Radiation source: fine-focus sealed tube	2653 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.880, T_max = 0.987	k = −15→15
7605 measured reflections	l = −18→18

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.225	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.1301P)² + 0.2413P] where P = (F_o² + 2F_c²)/3
3732 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 1.56 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₈H₁₇N₃S₂	γ = 96.191 (2)°
M_r = 339.47	V = 818.70 (3) Å³
Triclinic, P1	Z = 2
a = 5.1203 (1) Å	Mo Kα radiation
b = 11.9377 (3) Å	µ = 0.33 mm⁻¹
c = 14.1936 (4) Å	T = 100 K
α = 108.203 (2)°	0.40 × 0.08 × 0.04 mm
β = 90.230 (2)°

Data collection top

Bruker SMART APEX diffractometer	3732 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2653 reflections with I > 2σ(I)
T_min = 0.880, T_max = 0.987	R_int = 0.047
7605 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.225	H-atom parameters constrained
S = 1.13	Δρ_max = 1.56 e Å⁻³
3732 reflections	Δρ_min = −0.59 e Å⁻³
209 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.58962 (17)	0.85808 (8)	0.65532 (7)	0.0205 (3)
S2	0.72855 (18)	0.65218 (8)	0.48348 (7)	0.0221 (3)
N1	0.3474 (6)	0.6436 (3)	0.6054 (2)	0.0201 (7)
H1	0.3089	0.5687	0.5697	0.024*
N2	0.2021 (6)	0.6924 (3)	0.6868 (2)	0.0195 (7)
N3	−0.1582 (6)	0.7565 (3)	0.8569 (2)	0.0184 (7)
C1	0.9083 (7)	1.0499 (3)	0.6464 (3)	0.0215 (8)
C2	1.1083 (7)	1.1026 (3)	0.7164 (3)	0.0220 (8)
H2	1.2181	1.0543	0.7367	0.026*
C3	1.1524 (7)	1.2255 (4)	0.7581 (3)	0.0225 (8)
H3	1.2914	1.2608	0.8062	0.027*
C4	0.9918 (7)	1.2961 (3)	0.7288 (3)	0.0220 (8)
H4	1.0218	1.3801	0.7563	0.026*
C5	0.7885 (8)	1.2441 (4)	0.6596 (3)	0.0245 (8)
H5	0.6772	1.2924	0.6402	0.029*
C6	0.7460 (7)	1.1216 (4)	0.6183 (3)	0.0245 (8)
H6	0.6058	1.0864	0.5707	0.029*
C7	0.8657 (7)	0.9171 (3)	0.5981 (3)	0.0241 (8)
H7A	1.0257	0.8814	0.6075	0.029*
H7B	0.8278	0.8978	0.5260	0.029*
C8	0.5454 (7)	0.7094 (3)	0.5804 (3)	0.0172 (7)
C9	0.0151 (7)	0.6197 (3)	0.7016 (3)	0.0207 (8)
H9	−0.0098	0.5417	0.6557	0.025*
C10	−0.1597 (7)	0.6484 (3)	0.7829 (3)	0.0188 (8)
C11	0.0120 (8)	0.8667 (3)	0.8688 (3)	0.0256 (9)
H11A	0.1053	0.8922	0.9337	0.038*
H11B	−0.0949	0.9284	0.8643	0.038*
H11C	0.1397	0.8536	0.8163	0.038*
C12	−0.3503 (7)	0.7444 (3)	0.9212 (3)	0.0194 (8)
C13	−0.4243 (8)	0.8289 (4)	1.0078 (3)	0.0240 (8)
H13	−0.3371	0.9075	1.0304	0.029*
C14	−0.6278 (8)	0.7930 (4)	1.0584 (3)	0.0268 (9)
H14	−0.6825	0.8482	1.1170	0.032*
C15	−0.7569 (8)	0.6772 (4)	1.0260 (3)	0.0289 (9)
H15	−0.8972	0.6556	1.0628	0.035*
C16	−0.6840 (8)	0.5941 (4)	0.9418 (3)	0.0273 (9)
H16	−0.7720	0.5157	0.9206	0.033*
C17	−0.4769 (7)	0.6274 (3)	0.8878 (3)	0.0206 (8)
C18	−0.3533 (7)	0.5682 (3)	0.8002 (3)	0.0218 (8)
H18	−0.3958	0.4877	0.7605	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0212 (5)	0.0153 (5)	0.0253 (5)	0.0064 (3)	0.0069 (4)	0.0053 (4)
S2	0.0263 (5)	0.0180 (5)	0.0230 (5)	0.0078 (4)	0.0098 (4)	0.0060 (4)
N1	0.0221 (15)	0.0163 (15)	0.0211 (16)	0.0058 (12)	0.0055 (13)	0.0034 (12)
N2	0.0221 (15)	0.0181 (16)	0.0211 (16)	0.0090 (12)	0.0056 (13)	0.0081 (13)
N3	0.0220 (15)	0.0131 (15)	0.0230 (16)	0.0065 (12)	0.0057 (13)	0.0081 (12)
C1	0.0207 (18)	0.0182 (19)	0.027 (2)	0.0074 (14)	0.0118 (15)	0.0076 (15)
C2	0.0193 (18)	0.0203 (19)	0.030 (2)	0.0093 (14)	0.0061 (15)	0.0101 (16)
C3	0.0194 (18)	0.023 (2)	0.025 (2)	0.0051 (14)	0.0031 (15)	0.0075 (16)
C4	0.0253 (19)	0.0205 (19)	0.0228 (19)	0.0067 (15)	0.0096 (15)	0.0090 (15)
C5	0.029 (2)	0.023 (2)	0.028 (2)	0.0122 (16)	0.0087 (17)	0.0129 (16)
C6	0.0219 (19)	0.025 (2)	0.028 (2)	0.0079 (15)	0.0019 (16)	0.0074 (16)
C7	0.0189 (17)	0.021 (2)	0.033 (2)	0.0059 (14)	0.0093 (16)	0.0069 (16)
C8	0.0171 (16)	0.0173 (18)	0.0192 (17)	0.0078 (13)	0.0024 (14)	0.0069 (14)
C9	0.0236 (18)	0.0152 (18)	0.0247 (19)	0.0069 (14)	0.0022 (15)	0.0067 (15)
C10	0.0232 (18)	0.0152 (18)	0.0210 (18)	0.0064 (14)	0.0006 (15)	0.0086 (14)
C11	0.031 (2)	0.0130 (18)	0.033 (2)	0.0006 (15)	0.0061 (17)	0.0077 (16)
C12	0.0201 (17)	0.0182 (18)	0.0227 (19)	0.0066 (14)	0.0018 (15)	0.0089 (15)
C13	0.0257 (19)	0.022 (2)	0.025 (2)	0.0067 (15)	0.0031 (16)	0.0066 (16)
C14	0.028 (2)	0.031 (2)	0.023 (2)	0.0126 (16)	0.0058 (16)	0.0069 (17)
C15	0.0226 (19)	0.037 (2)	0.029 (2)	0.0038 (16)	0.0067 (16)	0.0126 (18)
C16	0.027 (2)	0.027 (2)	0.028 (2)	0.0010 (16)	0.0059 (17)	0.0098 (17)
C17	0.0214 (18)	0.0199 (19)	0.0227 (19)	0.0075 (14)	0.0029 (15)	0.0084 (15)
C18	0.0256 (19)	0.0168 (18)	0.0243 (19)	0.0055 (14)	0.0047 (15)	0.0073 (15)

Geometric parameters (Å, º) top

S1—C8	1.750 (4)	C6—H6	0.9500
S1—C7	1.818 (4)	C7—H7A	0.9900
S2—C8	1.673 (4)	C7—H7B	0.9900
N1—C8	1.332 (5)	C9—C10	1.442 (5)
N1—N2	1.382 (4)	C9—H9	0.9500
N1—H1	0.8800	C10—C18	1.380 (5)
N2—C9	1.284 (5)	C11—H11A	0.9800
N3—C12	1.371 (5)	C11—H11B	0.9800
N3—C10	1.386 (5)	C11—H11C	0.9800
N3—C11	1.460 (5)	C12—C17	1.409 (5)
C1—C2	1.377 (5)	C12—C13	1.409 (5)
C1—C6	1.395 (5)	C13—C14	1.374 (6)
C1—C7	1.509 (5)	C13—H13	0.9500
C2—C3	1.392 (5)	C14—C15	1.401 (6)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.387 (5)	C15—C16	1.377 (6)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.380 (6)	C16—C17	1.405 (6)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.388 (6)	C17—C18	1.415 (5)
C5—H5	0.9500	C18—H18	0.9500

C8—S1—C7	101.41 (18)	S2—C8—S1	124.0 (2)
C8—N1—N2	120.4 (3)	N2—C9—C10	124.5 (3)
C8—N1—H1	119.8	N2—C9—H9	117.7
N2—N1—H1	119.8	C10—C9—H9	117.7
C9—N2—N1	114.0 (3)	C18—C10—N3	109.2 (3)
C12—N3—C10	107.9 (3)	C18—C10—C9	123.9 (3)
C12—N3—C11	123.7 (3)	N3—C10—C9	126.9 (3)
C10—N3—C11	128.4 (3)	N3—C11—H11A	109.5
C2—C1—C6	118.9 (3)	N3—C11—H11B	109.5
C2—C1—C7	121.4 (3)	H11A—C11—H11B	109.5
C6—C1—C7	119.7 (4)	N3—C11—H11C	109.5
C1—C2—C3	121.1 (3)	H11A—C11—H11C	109.5
C1—C2—H2	119.5	H11B—C11—H11C	109.5
C3—C2—H2	119.5	N3—C12—C17	108.9 (3)
C4—C3—C2	119.5 (4)	N3—C12—C13	129.3 (4)
C4—C3—H3	120.2	C17—C12—C13	121.8 (4)
C2—C3—H3	120.2	C14—C13—C12	117.2 (4)
C5—C4—C3	119.9 (4)	C14—C13—H13	121.4
C5—C4—H4	120.1	C12—C13—H13	121.4
C3—C4—H4	120.1	C13—C14—C15	121.8 (4)
C4—C5—C6	120.2 (4)	C13—C14—H14	119.1
C4—C5—H5	119.9	C15—C14—H14	119.1
C6—C5—H5	119.9	C16—C15—C14	121.2 (4)
C5—C6—C1	120.3 (4)	C16—C15—H15	119.4
C5—C6—H6	119.8	C14—C15—H15	119.4
C1—C6—H6	119.8	C15—C16—C17	118.8 (4)
C1—C7—S1	108.2 (3)	C15—C16—H16	120.6
C1—C7—H7A	110.0	C17—C16—H16	120.6
S1—C7—H7A	110.0	C16—C17—C12	119.3 (4)
C1—C7—H7B	110.0	C16—C17—C18	134.3 (4)
S1—C7—H7B	110.0	C12—C17—C18	106.4 (3)
H7A—C7—H7B	108.4	C10—C18—C17	107.5 (3)
N1—C8—S2	121.5 (3)	C10—C18—H18	126.2
N1—C8—S1	114.4 (3)	C17—C18—H18	126.2

C8—N1—N2—C9	179.1 (3)	N2—C9—C10—C18	−177.4 (4)
C6—C1—C2—C3	−0.9 (6)	N2—C9—C10—N3	0.5 (6)
C7—C1—C2—C3	177.7 (4)	C10—N3—C12—C17	−0.2 (4)
C1—C2—C3—C4	0.2 (6)	C11—N3—C12—C17	179.8 (3)
C2—C3—C4—C5	0.7 (6)	C10—N3—C12—C13	179.8 (4)
C3—C4—C5—C6	−0.8 (6)	C11—N3—C12—C13	−0.2 (6)
C4—C5—C6—C1	0.0 (6)	N3—C12—C13—C14	179.4 (4)
C2—C1—C6—C5	0.8 (6)	C17—C12—C13—C14	−0.6 (6)
C7—C1—C6—C5	−177.8 (4)	C12—C13—C14—C15	0.3 (6)
C2—C1—C7—S1	102.5 (4)	C13—C14—C15—C16	0.2 (7)
C6—C1—C7—S1	−78.9 (4)	C14—C15—C16—C17	−0.3 (6)
C8—S1—C7—C1	172.9 (3)	C15—C16—C17—C12	0.0 (6)
N2—N1—C8—S2	178.8 (2)	C15—C16—C17—C18	−179.5 (4)
N2—N1—C8—S1	−2.4 (4)	N3—C12—C17—C16	−179.5 (3)
C7—S1—C8—N1	−179.1 (3)	C13—C12—C17—C16	0.5 (6)
C7—S1—C8—S2	−0.3 (3)	N3—C12—C17—C18	0.1 (4)
N1—N2—C9—C10	178.4 (3)	C13—C12—C17—C18	−179.9 (3)
C12—N3—C10—C18	0.2 (4)	N3—C10—C18—C17	−0.2 (4)
C11—N3—C10—C18	−179.8 (4)	C9—C10—C18—C17	178.1 (3)
C12—N3—C10—C9	−177.9 (3)	C16—C17—C18—C10	179.5 (4)
C11—N3—C10—C9	2.0 (6)	C12—C17—C18—C10	0.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2ⁱ	0.88	2.49	3.336 (3)	161

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇N₃S₂
M_r	339.47
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.1203 (1), 11.9377 (3), 14.1936 (4)
α, β, γ (°)	108.203 (2), 90.230 (2), 96.191 (2)
V (Å³)	818.70 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.40 × 0.08 × 0.04

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.880, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	7605, 3732, 2653
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.225, 1.13
No. of reflections	3732
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.56, −0.59

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2ⁱ	0.88	2.49	3.336 (3)	161

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank the University of Malaya for funding this study (Science Fund grants 12–02-03–2031, 12–02-03–2051).

References

Ali, M. A., Mirza, A. H., Hamid, M. H. S. A., Bujang, F. H. & Bernhardt, P. V. (2004). Polyhedron, 23, 2405–2412. Web of Science CSD CrossRef CAS Google Scholar
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