organic compounds
Benzyl N′-(1-methyl-1H-indol-3-ylmethylidene)hydrazinecarbodithioate
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The N′-(1-methyl-1H-indol-3-ylmethylidene)hydrazinecarbodithioate portion of the title molecule, C18H17N3S2, is nearly planar; this unit and the phenyl ring subtend an angle of 112.9 (2)° at the methylene C atom.
Related literature
For the structure of S-benzyl N-1-(1H-indol-3-ylmethylidenehydrazinecarbodithioate, see: Khaledi et al. (2008).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2007); cell 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).
Supporting information
10.1107/S1600536808039330/tk2334sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808039330/tk2334Isup2.hkl
N-Methylindole-3-carbaldehyde (1.59 g, 10 mmol) and S-benzyl dithiocarbazate (1.98 g, 10 mmol) were heated in ethanol (60 ml) for 1 h. Several drops of acetic acid were added. The solution yielded a solid on cooling. This was recrystallized from DMSO.
Hydrogen atoms were placed at calculated positions (C–H 0.95–0.99 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2 times Ueq(C), 1.5 for methyl-C. The amino H-atom was located in a difference Fourier map, and was refined with a distance restraint of N–H 0.88±0.01 Å; it does not form a hydrogen bond.
Data collection: APEX2 (Bruker, 2007); cell
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).Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C18H17N2S3 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. |
C18H17N3S2 | F(000) = 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 = 3.1–27.1° |
b = 6.1134 (2) Å | µ = 0.33 mm−1 |
c = 13.4961 (4) Å | T = 100 K |
β = 111.934 (2)° | 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) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 27.5°, θmin = 1.6° |
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 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: constr |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0366P)2 + 0.212P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
3277 reflections | Δρmax = 0.28 e Å−3 |
213 parameters | Δρmin = −0.28 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1261 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (8) |
C18H17N3S2 | V = 812.12 (5) Å3 |
Mr = 339.47 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 10.6111 (4) Å | µ = 0.33 mm−1 |
b = 6.1134 (2) Å | T = 100 K |
c = 13.4961 (4) Å | 0.30 × 0.10 × 0.02 mm |
β = 111.934 (2)° |
Bruker SMART APEX diffractometer | 3277 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2802 reflections with I > 2σ(I) |
Tmin = 0.908, Tmax = 0.993 | Rint = 0.027 |
5513 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.087 | Δρmax = 0.28 e Å−3 |
S = 1.03 | Δρmin = −0.28 e Å−3 |
3277 reflections | Absolute structure: Flack (1983), 1261 Friedel pairs |
213 parameters | Absolute structure parameter: 0.01 (8) |
2 restraints |
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) |
Experimental details
Crystal data | |
Chemical formula | C18H17N3S2 |
Mr | 339.47 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 100 |
a, b, c (Å) | 10.6111 (4), 6.1134 (2), 13.4961 (4) |
β (°) | 111.934 (2) |
V (Å3) | 812.12 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.30 × 0.10 × 0.02 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.908, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5513, 3277, 2802 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.087, 1.03 |
No. of reflections | 3277 |
No. of parameters | 213 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.28 |
Absolute structure | Flack (1983), 1261 Friedel pairs |
Absolute structure parameter | 0.01 (8) |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
Acknowledgements
We thank the University of Malaya for funding this study (Science Fund Grants 12–02-03–2031 & 12–02-03–2051).
References
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