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Acta Cryst. (2008). E64, o960    [ doi:10.1107/S1600536808011756 ]

2-Hydroxy-(2-methyl-1H-indol-3-ylmethylidene)benzohydrazide ethanol solvate

W. A. Yehye, A. Ariffin and S. W. Ng

Abstract top

In the title compound, C17H15N3O2·C2H6O, Schiff base molecules are linked by a hydroxy-amido hydrogen bond into a helical chain running along the b axis. This chain is consolidated by two other hydrogen bonds; the ethanol solvent molecule is a hydrogen-bond donor to the amide group and a hydrogen-bond acceptor for the indolyl NH group of an adjacent Schiff base molecule.

Comment top

There are no reports of the title Schiff base but there are several reports on the medicinal properties of the unsubstituted compound, indol-3-ylmethylidene-2-hydroxybenzohydrazide (Alemany et al., 1967; Fujikawa et al., 1966; Nakata et al., 1966; Singh et al., 1984). The methyl-substituted title compound (Scheme I, Fig. 1) is a planar molecule that is linked by a hydroxy···amido hydrogen bond into a helical chain that runs along the b-axis of the monoclinic unit cell (Fig. 2). The chain is consolidated by two other hydrogen bonds: the ethanol molecule is hydrogen-bond donor to the amido unit well as hydrogen-bond acceptor to the aminoindolyl unit of adjacent Schiff bases.

Related literature top

For reports on the medicinal properties of the unsubstituted compound, indol-3-ylmethylidene-2-hydroxybenzohydrazide, see: Alemany et al. (1967); Fujikawa et al. (1966); Nakata et al. (1966); Singh et al. (1984).

Experimental top

2-Hydroxybenzohyrazide (0.60 g, 4 mmol) and 2-methyl-1H-indole-3-carboxaldehyde (0.63 g, 4 mmol) were heated in ethanol (30 ml) for 3 h. The solvent was removed by evaporation and the light brown product recrystallized from ethanol.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5 U(C).

The oxygen- and nitrogen-bound H-atoms were also generated geometrically (O–H 0.84, N–H 0.88 Å).

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: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C17H15N3O2.C2H6O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius.
[Figure 2] Fig. 2. Hydrogen-bonded chain motif.
2-Hydroxy-(2-methyl-1H-indol-3-ylmethylidene)benzohydrazide ethanol solvate top
Crystal data top
C17H15N3O2·C2H6OF000 = 720
Mr = 339.39Dx = 1.304 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6771 reflections
a = 7.5907 (1) Åθ = 2.7–28.2º
b = 11.2269 (2) ŵ = 0.09 mm−1
c = 20.3014 (3) ÅT = 100 (2) K
β = 91.924 (1)ºPrism, yellow
V = 1729.11 (5) Å30.34 × 0.27 × 0.12 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		2869 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.056
Monochromator: graphiteθmax = 27.5º
T = 100(2) Kθmin = 2.0º
ω scansh = −9→9
Absorption correction: Nonek = −14→14
20827 measured reflectionsl = −26→22
3967 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.162  w = 1/[σ2(Fo2) + (0.0721P)2 + 0.9553P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.001
3967 reflectionsΔρmax = 0.31 e Å−3
230 parametersΔρmin = −0.30 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C17H15N3O2·C2H6OV = 1729.11 (5) Å3
Mr = 339.39Z = 4
Monoclinic, P21/cMo Kα
a = 7.5907 (1) ŵ = 0.09 mm−1
b = 11.2269 (2) ÅT = 100 (2) K
c = 20.3014 (3) Å0.34 × 0.27 × 0.12 mm
β = 91.924 (1)º
Data collection top
Bruker SMART APEX
diffractometer		3967 independent reflections
Absorption correction: None2869 reflections with I > 2σ(I)
20827 measured reflectionsRint = 0.056
Refinement top
R[F2 > 2σ(F2)] = 0.047230 parameters
wR(F2) = 0.162H-atom parameters constrained
S = 1.13Δρmax = 0.31 e Å−3
3967 reflectionsΔρmin = −0.30 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.60372 (18)0.39960 (12)0.26124 (6)0.0287 (3)
H1O0.64880.33420.25070.043*
O20.26721 (17)0.69310 (12)0.26809 (7)0.0272 (3)
O3−0.0963 (2)0.65666 (15)0.29094 (8)0.0409 (4)
H3O0.01260.66980.29160.061*
N10.3897 (2)0.53879 (15)0.32419 (7)0.0255 (4)
H1N0.45630.47460.32360.031*
N20.3081 (2)0.57121 (15)0.38183 (8)0.0263 (4)
N30.1852 (2)0.47451 (15)0.59623 (8)0.0265 (4)
H3N0.17300.43720.63390.032*
C10.5678 (2)0.46480 (17)0.20605 (9)0.0243 (4)
C20.6339 (3)0.43017 (18)0.14536 (10)0.0283 (4)
H20.70250.35970.14250.034*
C30.5997 (3)0.4978 (2)0.08976 (10)0.0313 (5)
H30.64620.47420.04890.038*
C40.4981 (3)0.60009 (19)0.09301 (10)0.0311 (4)
H40.47600.64710.05470.037*
C50.4291 (2)0.63320 (18)0.15254 (9)0.0270 (4)
H50.35830.70280.15450.032*
C60.4616 (2)0.56639 (17)0.20990 (9)0.0233 (4)
C70.3674 (2)0.60467 (17)0.26980 (9)0.0233 (4)
C80.3263 (2)0.49282 (18)0.42813 (9)0.0258 (4)
H80.38590.42040.41940.031*
C90.2589 (2)0.51224 (18)0.49235 (9)0.0258 (4)
C100.2617 (2)0.42767 (18)0.54211 (9)0.0266 (4)
C110.3331 (3)0.30424 (19)0.54307 (10)0.0324 (5)
H11A0.26720.25560.57390.049*
H11B0.45780.30600.55720.049*
H11C0.32120.26980.49880.049*
C120.1752 (2)0.61732 (18)0.51780 (9)0.0262 (4)
C130.1327 (3)0.73007 (19)0.49295 (10)0.0304 (4)
H130.16210.75170.44940.036*
C140.0472 (3)0.8094 (2)0.53269 (11)0.0343 (5)
H140.01850.88640.51610.041*
C150.0014 (3)0.7792 (2)0.59706 (11)0.0359 (5)
H15−0.05860.83560.62310.043*
C160.0425 (3)0.66914 (19)0.62286 (10)0.0314 (5)
H160.01230.64830.66640.038*
C170.1302 (2)0.58892 (18)0.58288 (9)0.0262 (4)
C18−0.1888 (3)0.7654 (2)0.28171 (11)0.0384 (5)
H18A−0.30590.75840.30140.046*
H18B−0.20770.77990.23390.046*
C19−0.0926 (3)0.8698 (2)0.31203 (13)0.0453 (6)
H19A−0.16760.94070.30880.068*
H19B0.01630.88390.28860.068*
H19C−0.06370.85290.35850.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0333 (8)0.0315 (7)0.0215 (7)0.0069 (6)0.0051 (5)0.0015 (6)
O20.0237 (7)0.0306 (7)0.0276 (7)0.0012 (5)0.0066 (5)0.0015 (6)
O30.0288 (8)0.0494 (10)0.0452 (10)−0.0007 (7)0.0132 (7)0.0105 (7)
N10.0239 (8)0.0333 (9)0.0198 (8)0.0029 (7)0.0060 (6)−0.0004 (7)
N20.0214 (8)0.0376 (9)0.0202 (8)−0.0009 (7)0.0053 (6)−0.0021 (7)
N30.0232 (8)0.0368 (9)0.0197 (8)−0.0011 (7)0.0043 (6)0.0004 (7)
C10.0210 (9)0.0310 (10)0.0209 (9)−0.0029 (7)0.0021 (7)0.0010 (7)
C20.0244 (9)0.0346 (10)0.0260 (10)0.0019 (8)0.0041 (7)−0.0026 (8)
C30.0292 (10)0.0440 (12)0.0211 (10)−0.0011 (9)0.0062 (8)−0.0014 (8)
C40.0327 (10)0.0399 (11)0.0208 (9)−0.0021 (9)0.0019 (8)0.0045 (8)
C50.0251 (9)0.0308 (10)0.0252 (10)−0.0008 (8)0.0021 (7)0.0016 (8)
C60.0194 (8)0.0302 (10)0.0205 (9)−0.0040 (7)0.0028 (7)−0.0016 (7)
C70.0185 (8)0.0279 (9)0.0236 (9)−0.0039 (7)0.0016 (7)−0.0004 (7)
C80.0192 (9)0.0341 (10)0.0242 (10)−0.0012 (7)0.0029 (7)−0.0017 (8)
C90.0173 (8)0.0379 (11)0.0224 (9)−0.0022 (7)0.0018 (7)−0.0010 (8)
C100.0184 (8)0.0391 (11)0.0224 (9)−0.0029 (8)0.0034 (7)−0.0018 (8)
C110.0308 (10)0.0400 (11)0.0268 (10)−0.0006 (9)0.0069 (8)0.0005 (9)
C120.0167 (8)0.0396 (11)0.0225 (9)−0.0030 (8)0.0022 (7)−0.0026 (8)
C130.0222 (9)0.0410 (11)0.0279 (10)−0.0020 (8)0.0021 (7)0.0017 (9)
C140.0264 (10)0.0362 (11)0.0402 (12)0.0025 (9)−0.0012 (9)0.0009 (9)
C150.0280 (10)0.0450 (12)0.0349 (11)0.0038 (9)0.0026 (8)−0.0087 (10)
C160.0238 (9)0.0447 (12)0.0258 (10)−0.0009 (8)0.0042 (8)−0.0055 (9)
C170.0177 (8)0.0382 (11)0.0226 (9)−0.0032 (7)0.0012 (7)−0.0020 (8)
C180.0253 (10)0.0568 (14)0.0332 (11)0.0033 (10)0.0047 (8)0.0130 (10)
C190.0292 (11)0.0548 (15)0.0520 (15)0.0108 (10)0.0026 (10)0.0041 (12)
Geometric parameters (Å, °) top
O1—C11.358 (2)C8—H80.9500
O1—H1O0.8400C9—C101.386 (3)
O2—C71.250 (2)C9—C121.444 (3)
O3—C181.417 (3)C10—C111.488 (3)
O3—H3O0.8400C11—H11A0.9800
N1—C71.335 (2)C11—H11B0.9800
N1—N21.391 (2)C11—H11C0.9800
N1—H1N0.8800C12—C131.396 (3)
N2—C81.292 (3)C12—C171.412 (3)
N3—C101.365 (2)C13—C141.379 (3)
N3—C171.375 (3)C13—H130.9500
N3—H3N0.8800C14—C151.405 (3)
C1—C61.401 (3)C14—H140.9500
C1—C21.401 (3)C15—C161.374 (3)
C2—C31.378 (3)C15—H150.9500
C2—H20.9500C16—C171.396 (3)
C3—C41.386 (3)C16—H160.9500
C3—H30.9500C18—C191.502 (4)
C4—C51.384 (3)C18—H18A0.9900
C4—H40.9500C18—H18B0.9900
C5—C61.400 (3)C19—H19A0.9800
C5—H50.9500C19—H19B0.9800
C6—C71.494 (3)C19—H19C0.9800
C8—C91.433 (3)
C1—O1—H1O109.5C9—C10—C11130.10 (18)
C18—O3—H3O109.5C10—C11—H11A109.5
C7—N1—N2120.20 (16)C10—C11—H11B109.5
C7—N1—H1N119.9H11A—C11—H11B109.5
N2—N1—H1N119.9C10—C11—H11C109.5
C8—N2—N1113.21 (16)H11A—C11—H11C109.5
C10—N3—C17109.62 (16)H11B—C11—H11C109.5
C10—N3—H3N125.2C13—C12—C17118.84 (18)
C17—N3—H3N125.2C13—C12—C9135.28 (18)
O1—C1—C6119.52 (16)C17—C12—C9105.88 (17)
O1—C1—C2120.54 (17)C14—C13—C12118.82 (19)
C6—C1—C2119.93 (17)C14—C13—H13120.6
C3—C2—C1120.29 (19)C12—C13—H13120.6
C3—C2—H2119.9C13—C14—C15121.6 (2)
C1—C2—H2119.9C13—C14—H14119.2
C2—C3—C4120.49 (19)C15—C14—H14119.2
C2—C3—H3119.8C16—C15—C14120.8 (2)
C4—C3—H3119.8C16—C15—H15119.6
C5—C4—C3119.45 (19)C14—C15—H15119.6
C5—C4—H4120.3C15—C16—C17117.72 (19)
C3—C4—H4120.3C15—C16—H16121.1
C4—C5—C6121.42 (19)C17—C16—H16121.1
C4—C5—H5119.3N3—C17—C16129.46 (18)
C6—C5—H5119.3N3—C17—C12108.30 (17)
C5—C6—C1118.38 (17)C16—C17—C12122.23 (19)
C5—C6—C7116.57 (17)O3—C18—C19112.73 (18)
C1—C6—C7124.88 (17)O3—C18—H18A109.0
O2—C7—N1121.54 (17)C19—C18—H18A109.0
O2—C7—C6120.86 (17)O3—C18—H18B109.0
N1—C7—C6117.57 (16)C19—C18—H18B109.0
N2—C8—C9121.71 (18)H18A—C18—H18B107.8
N2—C8—H8119.1C18—C19—H19A109.5
C9—C8—H8119.1C18—C19—H19B109.5
C10—C9—C8124.18 (18)H19A—C19—H19B109.5
C10—C9—C12107.16 (17)C18—C19—H19C109.5
C8—C9—C12128.66 (18)H19A—C19—H19C109.5
N3—C10—C9109.04 (18)H19B—C19—H19C109.5
N3—C10—C11120.86 (17)
C7—N1—N2—C8173.12 (16)C17—N3—C10—C11−179.95 (17)
O1—C1—C2—C3−178.81 (17)C8—C9—C10—N3−179.13 (17)
C6—C1—C2—C32.2 (3)C12—C9—C10—N3−0.1 (2)
C1—C2—C3—C4−0.7 (3)C8—C9—C10—C111.4 (3)
C2—C3—C4—C5−0.8 (3)C12—C9—C10—C11−179.53 (19)
C3—C4—C5—C60.8 (3)C10—C9—C12—C13−179.7 (2)
C4—C5—C6—C10.6 (3)C8—C9—C12—C13−0.7 (4)
C4—C5—C6—C7−174.79 (17)C10—C9—C12—C17−0.4 (2)
O1—C1—C6—C5178.89 (16)C8—C9—C12—C17178.61 (18)
C2—C1—C6—C5−2.1 (3)C17—C12—C13—C14−0.4 (3)
O1—C1—C6—C7−6.1 (3)C9—C12—C13—C14178.8 (2)
C2—C1—C6—C7172.88 (17)C12—C13—C14—C15−0.3 (3)
N2—N1—C7—O2−3.4 (3)C13—C14—C15—C160.7 (3)
N2—N1—C7—C6178.81 (15)C14—C15—C16—C17−0.2 (3)
C5—C6—C7—O2−1.0 (3)C10—N3—C17—C16178.45 (19)
C1—C6—C7—O2−176.05 (17)C10—N3—C17—C12−0.8 (2)
C5—C6—C7—N1176.83 (16)C15—C16—C17—N3−179.69 (19)
C1—C6—C7—N11.8 (3)C15—C16—C17—C12−0.5 (3)
N1—N2—C8—C9176.97 (16)C13—C12—C17—N3−179.82 (16)
N2—C8—C9—C10174.44 (18)C9—C12—C17—N30.7 (2)
N2—C8—C9—C12−4.4 (3)C13—C12—C17—C160.9 (3)
C17—N3—C10—C90.5 (2)C9—C12—C17—C16−178.58 (17)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.841.762.594 (2)176
O3—H3o···O20.842.022.843 (2)165
N1—H1n···O10.881.912.618 (2)136
N3—H3n···O3ii0.881.962.824 (2)168
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.841.762.594 (2)176
O3—H3o···O20.842.022.843 (2)165
N1—H1n···O10.881.912.618 (2)136
N3—H3n···O3ii0.881.962.824 (2)168
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, −y+1, −z+1.
Acknowledgements top

We acknowledge the SAGA grant (06–02-03–0147) for support of this study, and the University of Malaya for the purchase of the diffractometer.

references
References top

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Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Fujikawa, F., Yamashita, I., Seno, T., Sasaki, M., Naito, M. & Tsukuma, S. (1966). Yakugaku Zasshi, 86, 801–804.

Nakata, H., Harada, H. & Hirata, Y. (1966). Tetrahedron Lett. pp. 2515–2522.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Singh, I. P., Gurtu, S., Kumar, A., Sinha, J. N., Bhargava, K. P. & Shanker, K. (1984). Archiv Pharm. (Weinheim), 317, 609–614.

Westrip, S. P. (2008). publCIF. In preparation.