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

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

doi:10.1107/S1600536808038609

organic compounds

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Volume 64| Part 12| December 2008| Page o2445

doi:10.1107/S1600536808038609

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

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 crystal of the title compound, C₁₇H₁₅N₃S₂·0.5C₂H₆O, the molecules are linked by a pair of N—H_aliphatic⋯S hydrogen bonds across a center of inversion, forming a dimer. The ethanol solvent molecule, which is statistically disordered about a crystallographic twofold rotation axis, accepts an N—H_aromatic⋯O hydrogen bond; the hydroxy group of the solvent molecule is not engaged in hydrogen bonding.

Related literature

For references to benzyl esters of hydrazinecarbodithioic acids, see: Khaledi et al. (2008 ).

Experimental

Crystal data

C₁₇H₁₅N₃S₂·0.5C₂H₆O
M_r = 348.47
Monoclinic, C 2/c
a = 13.4225 (2) Å
b = 15.4088 (2) Å
c = 16.8120 (3) Å
β = 102.637 (1)°
V = 3392.90 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 100 (2) K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.924, T_max = 0.954
14302 measured reflections
3897 independent reflections
3332 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.088
S = 1.03
3897 reflections
232 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯S2ⁱ	0.88 (1)	2.52 (1)	3.350 (1)	159 (2)
N3—H3n⋯O1	0.87 (1)	2.25 (1)	3.047 (3)	153 (2)
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/S1600536808038609/hb2851sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038609/hb2851Isup2.hkl

checkCIF report

Comment top

For background references, see: Khaledi et al. (2008).

Related literature top

For references to benzyl esters of hydrazinecarbodithioic acids, see: Khaledi et al. (2008).

Experimental top

Indole-2-carbaldehyde (0.36 g, 2.5 mmol) and S-benzyldithiocarbazate (0.495 g, 2.5 mmol) were heated in ethanol (40 ml) for 3 h. The solution was set aside for the formation of yellow blocks of (I).

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. View of (I) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Only one orientation of the ethanol molecule is shown.

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

Crystal data top

C₁₇H₁₅N₃S₂·0.5C₂H₆O	F(000) = 1464
M_r = 348.47	D_x = 1.364 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5259 reflections
a = 13.4225 (2) Å	θ = 2.5–28.3°
b = 15.4088 (2) Å	µ = 0.32 mm⁻¹
c = 16.8120 (3) Å	T = 100 K
β = 102.637 (1)°	Block, yellow
V = 3392.90 (9) Å³	0.25 × 0.20 × 0.15 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	3897 independent reflections
Radiation source: fine-focus sealed tube	3332 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→17
T_min = 0.924, T_max = 0.954	k = −19→20
14302 measured reflections	l = −21→17

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0411P)² + 3.3308P] where P = (F_o² + 2F_c²)/3
3897 reflections	(Δ/σ)_max = 0.001
232 parameters	Δρ_max = 0.35 e Å⁻³
5 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₇H₁₅N₃S₂·0.5C₂H₆O	V = 3392.90 (9) Å³
M_r = 348.47	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 13.4225 (2) Å	µ = 0.32 mm⁻¹
b = 15.4088 (2) Å	T = 100 K
c = 16.8120 (3) Å	0.25 × 0.20 × 0.15 mm
β = 102.637 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	3897 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3332 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.954	R_int = 0.028
14302 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	5 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.35 e Å⁻³
3897 reflections	Δρ_min = −0.40 e Å⁻³
232 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.58648 (3)	0.69507 (2)	0.36508 (2)	0.01972 (10)
S2	0.56141 (3)	0.50160 (2)	0.38844 (2)	0.02263 (11)
N1	0.48149 (10)	0.62574 (8)	0.46106 (8)	0.0201 (3)
H1N	0.4612 (15)	0.5843 (10)	0.4893 (11)	0.036 (5)*
N2	0.45977 (10)	0.71147 (8)	0.47237 (8)	0.0200 (3)
N3	0.39716 (10)	0.88130 (8)	0.48940 (8)	0.0205 (3)
H3N	0.4341 (14)	0.8771 (13)	0.4528 (10)	0.039 (6)*
C1	0.72885 (12)	0.71544 (9)	0.27832 (9)	0.0199 (3)
C2	0.83286 (12)	0.71386 (11)	0.31290 (10)	0.0254 (3)
H2	0.8608	0.6671	0.3476	0.031*
C3	0.89612 (13)	0.77961 (12)	0.29733 (10)	0.0297 (4)
H3	0.9671	0.7776	0.3212	0.036*
C4	0.85687 (13)	0.84829 (11)	0.24721 (10)	0.0260 (3)
H4	0.9004	0.8937	0.2372	0.031*
C5	0.75366 (13)	0.85010 (10)	0.21189 (10)	0.0242 (3)
H5	0.7263	0.8968	0.1770	0.029*
C6	0.68972 (12)	0.78405 (9)	0.22712 (10)	0.0222 (3)
H6	0.6190	0.7858	0.2024	0.027*
C7	0.66018 (12)	0.64525 (9)	0.29845 (10)	0.0211 (3)
H7A	0.7011	0.5962	0.3264	0.025*
H7B	0.6144	0.6232	0.2482	0.025*
C8	0.53949 (11)	0.60480 (9)	0.40842 (9)	0.0180 (3)
C9	0.40256 (11)	0.72590 (9)	0.52304 (9)	0.0203 (3)
H9	0.3811	0.6794	0.5524	0.024*
C10	0.37149 (11)	0.81355 (9)	0.53466 (9)	0.0197 (3)
C11	0.31225 (12)	0.84426 (9)	0.58549 (9)	0.0208 (3)
H11	0.2848	0.8111	0.6233	0.025*
C12	0.29954 (11)	0.93534 (9)	0.57094 (9)	0.0192 (3)
C13	0.35401 (11)	0.95615 (9)	0.51045 (9)	0.0197 (3)
C14	0.35929 (12)	1.04048 (10)	0.48156 (10)	0.0246 (3)
H14	0.3960	1.0533	0.4407	0.030*
C15	0.30886 (13)	1.10461 (10)	0.51477 (10)	0.0269 (4)
H15	0.3116	1.1628	0.4967	0.032*
C16	0.25378 (13)	1.08549 (10)	0.57456 (10)	0.0259 (3)
H16	0.2196	1.1309	0.5960	0.031*
C17	0.24827 (12)	1.00197 (10)	0.60284 (10)	0.0229 (3)
H17	0.2105	0.9897	0.6431	0.027*
O1	0.48913 (18)	0.92618 (16)	0.34417 (14)	0.0289 (5)	0.50
H1O	0.5523 (10)	0.922 (3)	0.363 (3)	0.045 (13)*	0.50
C18	0.4709 (7)	1.0002 (6)	0.2875 (4)	0.0472 (9)	0.50
H18A	0.3966	1.0099	0.2687	0.057*	0.50
H18B	0.5016	1.0533	0.3157	0.057*	0.50
C19	0.5162 (7)	0.9824 (6)	0.2172 (4)	0.0472 (9)	0.50
H19A	0.5044	1.0320	0.1798	0.071*	0.50
H19B	0.4847	0.9304	0.1888	0.071*	0.50
H19C	0.5898	0.9729	0.2360	0.071*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0245 (2)	0.01412 (17)	0.0230 (2)	0.00081 (13)	0.01047 (15)	0.00013 (13)
S2	0.0342 (2)	0.01388 (17)	0.0233 (2)	−0.00028 (14)	0.01385 (17)	−0.00209 (14)
N1	0.0271 (7)	0.0148 (6)	0.0210 (7)	0.0021 (5)	0.0108 (5)	0.0004 (5)
N2	0.0225 (6)	0.0171 (6)	0.0203 (7)	0.0026 (5)	0.0042 (5)	−0.0024 (5)
N3	0.0223 (6)	0.0210 (6)	0.0204 (7)	0.0009 (5)	0.0092 (5)	−0.0024 (5)
C1	0.0255 (8)	0.0185 (7)	0.0183 (7)	−0.0008 (6)	0.0104 (6)	−0.0024 (5)
C2	0.0261 (8)	0.0299 (8)	0.0217 (8)	0.0038 (6)	0.0082 (7)	0.0082 (6)
C3	0.0207 (8)	0.0439 (10)	0.0241 (9)	−0.0035 (7)	0.0045 (7)	0.0074 (7)
C4	0.0293 (9)	0.0299 (8)	0.0202 (8)	−0.0086 (7)	0.0087 (7)	0.0026 (6)
C5	0.0316 (9)	0.0207 (7)	0.0204 (8)	−0.0001 (6)	0.0062 (7)	0.0028 (6)
C6	0.0229 (8)	0.0213 (7)	0.0222 (8)	−0.0002 (6)	0.0044 (6)	−0.0009 (6)
C7	0.0258 (8)	0.0179 (7)	0.0221 (8)	0.0001 (6)	0.0110 (6)	−0.0025 (6)
C8	0.0199 (7)	0.0170 (6)	0.0169 (7)	−0.0003 (5)	0.0031 (6)	0.0001 (5)
C9	0.0224 (7)	0.0199 (7)	0.0182 (7)	0.0022 (6)	0.0038 (6)	−0.0003 (6)
C10	0.0199 (7)	0.0209 (7)	0.0178 (7)	0.0013 (6)	0.0028 (6)	−0.0012 (6)
C11	0.0242 (8)	0.0206 (7)	0.0181 (8)	0.0021 (6)	0.0057 (6)	−0.0003 (6)
C12	0.0184 (7)	0.0217 (7)	0.0164 (7)	0.0012 (6)	0.0014 (6)	−0.0025 (6)
C13	0.0187 (7)	0.0209 (7)	0.0190 (8)	0.0007 (6)	0.0032 (6)	−0.0043 (6)
C14	0.0281 (8)	0.0227 (7)	0.0235 (8)	−0.0033 (6)	0.0066 (7)	−0.0018 (6)
C15	0.0333 (9)	0.0183 (7)	0.0270 (9)	0.0001 (6)	0.0017 (7)	−0.0020 (6)
C16	0.0265 (8)	0.0234 (7)	0.0262 (9)	0.0053 (6)	0.0020 (7)	−0.0082 (6)
C17	0.0224 (8)	0.0263 (8)	0.0203 (8)	0.0030 (6)	0.0057 (6)	−0.0046 (6)
O1	0.0238 (12)	0.0401 (13)	0.0217 (12)	−0.0033 (10)	0.0026 (10)	0.0035 (10)
C18	0.041 (2)	0.050 (3)	0.0478 (15)	0.0096 (19)	0.0033 (12)	−0.001 (2)
C19	0.041 (2)	0.050 (3)	0.0478 (15)	0.0096 (19)	0.0033 (12)	−0.001 (2)

Geometric parameters (Å, º) top

S1—C8	1.7506 (15)	C9—C10	1.439 (2)
S1—C7	1.8187 (15)	C9—H9	0.9500
S2—C8	1.6647 (14)	C10—C11	1.372 (2)
N1—C8	1.3397 (19)	C11—C12	1.428 (2)
N1—N2	1.3748 (16)	C11—H11	0.9500
N1—H1N	0.875 (9)	C12—C17	1.406 (2)
N2—C9	1.285 (2)	C12—C13	1.413 (2)
N3—C13	1.3713 (18)	C13—C14	1.394 (2)
N3—C10	1.3792 (19)	C14—C15	1.383 (2)
N3—H3N	0.873 (9)	C14—H14	0.9500
C1—C2	1.390 (2)	C15—C16	1.403 (2)
C1—C6	1.392 (2)	C15—H15	0.9500
C1—C7	1.507 (2)	C16—C17	1.379 (2)
C2—C3	1.383 (2)	C16—H16	0.9500
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.383 (2)	O1—C18	1.472 (8)
C3—H3	0.9500	O1—H1O	0.839 (10)
C4—C5	1.383 (2)	C18—C19	1.469 (5)
C4—H4	0.9500	C18—H18A	0.9900
C5—C6	1.391 (2)	C18—H18B	0.9900
C5—H5	0.9500	C19—H19A	0.9800
C6—H6	0.9500	C19—H19B	0.9800
C7—H7A	0.9900	C19—H19C	0.9800
C7—H7B	0.9900

C8—S1—C7	102.42 (7)	C11—C10—N3	109.34 (13)
C8—N1—N2	119.62 (12)	C11—C10—C9	129.24 (14)
C8—N1—H1N	118.6 (13)	N3—C10—C9	121.37 (14)
N2—N1—H1N	121.7 (13)	C10—C11—C12	107.22 (13)
C9—N2—N1	115.70 (13)	C10—C11—H11	126.4
C13—N3—C10	108.88 (12)	C12—C11—H11	126.4
C13—N3—H3N	125.6 (14)	C17—C12—C13	118.83 (14)
C10—N3—H3N	125.5 (14)	C17—C12—C11	134.62 (15)
C2—C1—C6	118.72 (14)	C13—C12—C11	106.55 (13)
C2—C1—C7	120.08 (14)	N3—C13—C14	129.59 (14)
C6—C1—C7	121.17 (14)	N3—C13—C12	108.01 (13)
C3—C2—C1	120.66 (15)	C14—C13—C12	122.40 (14)
C3—C2—H2	119.7	C15—C14—C13	117.29 (15)
C1—C2—H2	119.7	C15—C14—H14	121.4
C4—C3—C2	120.53 (15)	C13—C14—H14	121.4
C4—C3—H3	119.7	C14—C15—C16	121.36 (15)
C2—C3—H3	119.7	C14—C15—H15	119.3
C3—C4—C5	119.29 (15)	C16—C15—H15	119.3
C3—C4—H4	120.4	C17—C16—C15	121.27 (14)
C5—C4—H4	120.4	C17—C16—H16	119.4
C4—C5—C6	120.45 (15)	C15—C16—H16	119.4
C4—C5—H5	119.8	C16—C17—C12	118.83 (15)
C6—C5—H5	119.8	C16—C17—H17	120.6
C5—C6—C1	120.35 (15)	C12—C17—H17	120.6
C5—C6—H6	119.8	C18—O1—H1O	108 (3)
C1—C6—H6	119.8	C19—C18—O1	109.7 (7)
C1—C7—S1	106.10 (10)	C19—C18—H18A	109.7
C1—C7—H7A	110.5	O1—C18—H18A	109.7
S1—C7—H7A	110.5	C19—C18—H18B	109.7
C1—C7—H7B	110.5	O1—C18—H18B	109.7
S1—C7—H7B	110.5	H18A—C18—H18B	108.2
H7A—C7—H7B	108.7	C18—C19—H19A	109.5
N1—C8—S2	121.15 (11)	C18—C19—H19B	109.5
N1—C8—S1	113.45 (10)	H19A—C19—H19B	109.5
S2—C8—S1	125.40 (9)	C18—C19—H19C	109.5
N2—C9—C10	119.03 (14)	H19A—C19—H19C	109.5
N2—C9—H9	120.5	H19B—C19—H19C	109.5
C10—C9—H9	120.5

C8—N1—N2—C9	179.09 (14)	N2—C9—C10—C11	−179.23 (16)
C6—C1—C2—C3	0.6 (2)	N2—C9—C10—N3	3.6 (2)
C7—C1—C2—C3	−177.57 (15)	N3—C10—C11—C12	0.47 (17)
C1—C2—C3—C4	0.2 (3)	C9—C10—C11—C12	−176.97 (15)
C2—C3—C4—C5	−0.8 (3)	C10—C11—C12—C17	179.98 (17)
C3—C4—C5—C6	0.6 (2)	C10—C11—C12—C13	−0.39 (17)
C4—C5—C6—C1	0.2 (2)	C10—N3—C13—C14	179.53 (16)
C2—C1—C6—C5	−0.8 (2)	C10—N3—C13—C12	0.12 (17)
C7—C1—C6—C5	177.36 (14)	C17—C12—C13—N3	179.86 (13)
C2—C1—C7—S1	106.98 (14)	C11—C12—C13—N3	0.16 (16)
C6—C1—C7—S1	−71.14 (16)	C17—C12—C13—C14	0.4 (2)
C8—S1—C7—C1	−163.14 (11)	C11—C12—C13—C14	−179.30 (14)
N2—N1—C8—S2	−176.00 (11)	N3—C13—C14—C15	−179.11 (15)
N2—N1—C8—S1	3.72 (18)	C12—C13—C14—C15	0.2 (2)
C7—S1—C8—N1	179.96 (11)	C13—C14—C15—C16	−0.6 (2)
C7—S1—C8—S2	−0.33 (12)	C14—C15—C16—C17	0.3 (3)
N1—N2—C9—C10	−176.43 (13)	C15—C16—C17—C12	0.3 (2)
C13—N3—C10—C11	−0.38 (17)	C13—C12—C17—C16	−0.7 (2)
C13—N3—C10—C9	177.30 (13)	C11—C12—C17—C16	178.94 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···S2ⁱ	0.88 (1)	2.52 (1)	3.350 (1)	159 (2)
N3—H3n···O1	0.87 (1)	2.25 (1)	3.047 (3)	153 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅N₃S₂·0.5C₂H₆O
M_r	348.47
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	13.4225 (2), 15.4088 (2), 16.8120 (3)
β (°)	102.637 (1)
V (Å³)	3392.90 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.924, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	14302, 3897, 3332
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.088, 1.03
No. of reflections	3897
No. of parameters	232
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.40

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—H1n···S2ⁱ	0.88 (1)	2.52 (1)	3.350 (1)	159 (2)
N3—H3n···O1	0.87 (1)	2.25 (1)	3.047 (3)	153 (2)

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

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2430. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

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Volume 64| Part 12| December 2008| Page o2445

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

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Experimental

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organic compounds

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