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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1920.
Published online 2009 July 18. doi:  10.1107/S1600536809027032
PMCID: PMC2977291

3,4,5-Trihydr­oxy-N′-[(1-methyl-1H-indol-2-yl)methyl­idene]benzohydrazide

Abstract

The structure of the title compound, C17H15N3O4, displays inter­molecular O—H(...)N and O—H(...)O hydrogen bonding between adjacent mol­ecules. Intra­molecular O—H(...)O hydrogen bonds also occur. The molecule is essentially planar with a deviation of 0.090 (1) Å from the best plane running through the connected ring systems.

Related literature

For related compounds see: Khaledi et al. (2008a [triangle],b [triangle], 2009 [triangle]).

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Object name is e-65-o1920-scheme1.jpg

Experimental

Crystal data

  • C17H15N3O4
  • M r = 325.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1920-efi1.jpg
  • a = 9.0839 (2) Å
  • b = 13.1684 (3) Å
  • c = 12.4414 (3) Å
  • β = 104.2740 (10)°
  • V = 1442.30 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 100 K
  • 0.49 × 0.16 × 0.09 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.948, T max = 0.991
  • 10177 measured reflections
  • 4070 independent reflections
  • 3153 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.127
  • S = 0.99
  • 4070 reflections
  • 221 parameters
  • H-atom parameters constrained
  • Δρmax = 0.63 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027032/hg2532sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027032/hg2532Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the University of Malaya for funding this study (FRGS grant No. FP009/2008 C).

supplementary crystallographic information

Experimental

A mixture of 1-Methylindole-2-carboxaldehyde (0.80 g, 5 mmol) and 3,4,5-trihydroxybenzoylhydrazine(0.92 g, 5 mmol) in the presence of acetic acid (1 ml) was heated in ethanol (70 ml) for 6 h. The solution was then cooled and filtered to remove the unreacted hydrazine. The filtrate was poured to water (400 ml), the solid product formed were filtered off, washed with diethyl ether,and dried in an oven. Suitable crystals for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature.

Refinement

All Hydrogen atoms were placed at calculated positions (C—H 0.95–0.98, N—H 0.88 and O—H 0.84 Å), with U(H) set to 1.2–1.5 times Ueq(C,N,O).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the title compound at 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C17H15N3O4F(000) = 680
Mr = 325.32Dx = 1.498 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3739 reflections
a = 9.0839 (2) Åθ = 2.3–30.4°
b = 13.1684 (3) ŵ = 0.11 mm1
c = 12.4414 (3) ÅT = 100 K
β = 104.274 (1)°Block, green
V = 1442.30 (6) Å30.49 × 0.16 × 0.09 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer4070 independent reflections
Radiation source: fine-focus sealed tube3153 reflections with I > 2σ(I)
graphiteRint = 0.019
ω scansθmax = 30.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→12
Tmin = 0.948, Tmax = 0.991k = −18→18
10177 measured reflectionsl = −17→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0672P)2 + 0.9156P] where P = (Fo2 + 2Fc2)/3
4070 reflections(Δ/σ)max < 0.001
221 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = −0.26 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
N10.47487 (13)0.36671 (9)0.05923 (10)0.0132 (2)
H1N0.46550.3333−0.00340.016*
N20.38051 (13)0.44784 (9)0.06479 (10)0.0134 (2)
N30.06173 (13)0.56577 (9)−0.13005 (10)0.0151 (2)
O10.99391 (12)0.12533 (8)0.33141 (8)0.0165 (2)
H1O1.02190.06450.33130.025*
O20.98618 (11)0.01716 (7)0.13104 (8)0.0149 (2)
H2O0.9766−0.03050.17370.022*
O30.77044 (12)0.07206 (8)−0.05744 (8)0.0189 (2)
H3O0.84730.0349−0.05060.028*
O40.59664 (13)0.38379 (8)0.23996 (8)0.0199 (2)
C10.04811 (18)0.51469 (13)−0.23489 (13)0.0226 (3)
H1A−0.04260.5393−0.28870.034*
H1B0.03930.4413−0.22470.034*
H1C0.13830.5288−0.26230.034*
C2−0.02892 (15)0.64421 (11)−0.11137 (12)0.0155 (3)
C3−0.15129 (16)0.69271 (11)−0.18421 (13)0.0192 (3)
H3−0.18340.6736−0.26000.023*
C4−0.22304 (17)0.76936 (12)−0.14091 (14)0.0213 (3)
H4−0.30590.8039−0.18830.026*
C5−0.17667 (17)0.79760 (11)−0.02853 (14)0.0219 (3)
H5−0.22910.8505−0.00160.026*
C6−0.05636 (17)0.74988 (11)0.04323 (13)0.0195 (3)
H6−0.02590.76920.11910.023*
C70.02010 (16)0.67213 (11)0.00177 (12)0.0163 (3)
C80.14341 (16)0.60759 (11)0.05098 (12)0.0162 (3)
H80.19970.60850.12630.019*
C90.16628 (15)0.54349 (10)−0.03077 (11)0.0137 (3)
C100.27384 (15)0.46201 (10)−0.02389 (11)0.0134 (3)
H100.26620.4180−0.08560.016*
C110.58127 (15)0.33924 (10)0.15038 (11)0.0129 (3)
C120.68091 (14)0.25165 (10)0.13972 (11)0.0123 (3)
C130.78798 (15)0.22437 (10)0.23633 (11)0.0132 (3)
H130.79170.25970.30350.016*
C140.88907 (15)0.14590 (10)0.23472 (11)0.0128 (3)
C150.88441 (15)0.09305 (10)0.13689 (11)0.0122 (2)
C160.77684 (15)0.12083 (10)0.04008 (11)0.0135 (3)
C170.67475 (15)0.19925 (10)0.04105 (11)0.0143 (3)
H170.60140.2171−0.02490.017*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0140 (5)0.0112 (5)0.0140 (5)0.0024 (4)0.0029 (4)−0.0013 (4)
N20.0120 (5)0.0110 (5)0.0173 (5)0.0015 (4)0.0040 (4)0.0006 (4)
N30.0132 (5)0.0141 (5)0.0174 (6)0.0019 (4)0.0028 (4)0.0011 (4)
O10.0180 (5)0.0172 (5)0.0121 (4)0.0047 (4)−0.0006 (4)0.0011 (4)
O20.0183 (5)0.0122 (5)0.0157 (5)0.0049 (4)0.0069 (4)0.0039 (4)
O30.0196 (5)0.0214 (5)0.0139 (5)0.0075 (4)0.0010 (4)−0.0046 (4)
O40.0232 (5)0.0203 (5)0.0151 (5)0.0068 (4)0.0027 (4)−0.0035 (4)
C10.0219 (7)0.0248 (8)0.0192 (7)0.0035 (6)0.0014 (6)−0.0027 (6)
C20.0135 (6)0.0124 (6)0.0219 (7)0.0001 (5)0.0066 (5)0.0025 (5)
C30.0148 (6)0.0182 (7)0.0247 (7)0.0009 (5)0.0050 (5)0.0049 (6)
C40.0151 (6)0.0168 (7)0.0325 (8)0.0031 (5)0.0070 (6)0.0071 (6)
C50.0185 (7)0.0134 (6)0.0370 (9)0.0020 (5)0.0128 (6)0.0013 (6)
C60.0193 (7)0.0154 (7)0.0263 (8)−0.0008 (5)0.0101 (6)−0.0018 (5)
C70.0149 (6)0.0129 (6)0.0220 (7)−0.0004 (5)0.0068 (5)0.0009 (5)
C80.0155 (6)0.0142 (6)0.0197 (7)0.0003 (5)0.0061 (5)0.0004 (5)
C90.0122 (6)0.0123 (6)0.0165 (6)−0.0002 (5)0.0034 (5)0.0022 (5)
C100.0125 (6)0.0126 (6)0.0155 (6)−0.0008 (5)0.0042 (5)−0.0007 (5)
C110.0134 (6)0.0121 (6)0.0135 (6)0.0001 (5)0.0042 (5)0.0011 (5)
C120.0122 (6)0.0116 (6)0.0131 (6)0.0007 (4)0.0031 (5)0.0013 (5)
C130.0148 (6)0.0131 (6)0.0120 (6)0.0008 (5)0.0034 (5)−0.0004 (5)
C140.0131 (6)0.0132 (6)0.0117 (6)0.0001 (5)0.0022 (4)0.0029 (5)
C150.0120 (6)0.0111 (6)0.0142 (6)0.0012 (4)0.0042 (5)0.0020 (5)
C160.0147 (6)0.0142 (6)0.0120 (6)0.0006 (5)0.0038 (5)−0.0016 (5)
C170.0142 (6)0.0147 (6)0.0129 (6)0.0025 (5)0.0013 (5)0.0007 (5)

Geometric parameters (Å, °)

N1—C111.3455 (17)C4—C51.407 (2)
N1—N21.3821 (15)C4—H40.9500
N1—H1N0.8800C5—C61.380 (2)
N2—C101.2900 (17)C5—H50.9500
N3—C21.3760 (18)C6—C71.405 (2)
N3—C91.3912 (17)C6—H60.9500
N3—C11.4455 (19)C7—C81.419 (2)
O1—C141.3647 (16)C8—C91.376 (2)
O1—H1O0.8400C8—H80.9500
O2—C151.3755 (16)C9—C101.4394 (19)
O2—H2O0.8400C10—H100.9500
O3—C161.3613 (16)C11—C121.4921 (18)
O3—H3O0.8400C12—C131.3941 (18)
O4—C111.2365 (17)C12—C171.3972 (18)
C1—H1A0.9800C13—C141.3859 (18)
C1—H1B0.9800C13—H130.9500
C1—H1C0.9800C14—C151.3936 (18)
C2—C31.403 (2)C15—C161.3995 (18)
C2—C71.416 (2)C16—C171.3900 (19)
C3—C41.381 (2)C17—H170.9500
C3—H30.9500
C11—N1—N2119.41 (11)C6—C7—C8133.41 (14)
C11—N1—H1N120.3C2—C7—C8107.14 (12)
N2—N1—H1N120.3C9—C8—C7107.18 (13)
C10—N2—N1114.41 (11)C9—C8—H8126.4
C2—N3—C9108.32 (12)C7—C8—H8126.4
C2—N3—C1125.46 (12)C8—C9—N3109.41 (12)
C9—N3—C1126.22 (12)C8—C9—C10129.58 (13)
C14—O1—H1O109.5N3—C9—C10120.98 (12)
C15—O2—H2O109.5N2—C10—C9120.95 (13)
C16—O3—H3O109.5N2—C10—H10119.5
N3—C1—H1A109.5C9—C10—H10119.5
N3—C1—H1B109.5O4—C11—N1122.01 (12)
H1A—C1—H1B109.5O4—C11—C12120.71 (12)
N3—C1—H1C109.5N1—C11—C12117.28 (12)
H1A—C1—H1C109.5C13—C12—C17119.91 (12)
H1B—C1—H1C109.5C13—C12—C11115.60 (12)
N3—C2—C3130.13 (14)C17—C12—C11124.48 (12)
N3—C2—C7107.95 (12)C14—C13—C12120.23 (12)
C3—C2—C7121.92 (13)C14—C13—H13119.9
C4—C3—C2117.12 (14)C12—C13—H13119.9
C4—C3—H3121.4O1—C14—C13117.13 (12)
C2—C3—H3121.4O1—C14—C15122.35 (12)
C3—C4—C5121.76 (14)C13—C14—C15120.49 (12)
C3—C4—H4119.1O2—C15—C14122.20 (12)
C5—C4—H4119.1O2—C15—C16118.70 (12)
C6—C5—C4121.17 (14)C14—C15—C16119.04 (12)
C6—C5—H5119.4O3—C16—C17118.44 (12)
C4—C5—H5119.4O3—C16—C15120.73 (12)
C5—C6—C7118.60 (15)C17—C16—C15120.83 (12)
C5—C6—H6120.7C16—C17—C12119.49 (12)
C7—C6—H6120.7C16—C17—H17120.3
C6—C7—C2119.43 (13)C12—C17—H17120.3
C11—N1—N2—C10−173.94 (12)C8—C9—C10—N2−9.1 (2)
C9—N3—C2—C3−179.04 (14)N3—C9—C10—N2172.91 (13)
C1—N3—C2—C30.1 (2)N2—N1—C11—O40.8 (2)
C9—N3—C2—C70.29 (15)N2—N1—C11—C12−179.57 (11)
C1—N3—C2—C7179.39 (13)O4—C11—C12—C130.73 (19)
N3—C2—C3—C4179.14 (14)N1—C11—C12—C13−178.95 (12)
C7—C2—C3—C4−0.1 (2)O4—C11—C12—C17−177.78 (13)
C2—C3—C4—C5−0.4 (2)N1—C11—C12—C172.5 (2)
C3—C4—C5—C60.3 (2)C17—C12—C13—C140.5 (2)
C4—C5—C6—C70.2 (2)C11—C12—C13—C14−178.13 (12)
C5—C6—C7—C2−0.7 (2)C12—C13—C14—O1177.99 (12)
C5—C6—C7—C8−178.83 (15)C12—C13—C14—C15−0.4 (2)
N3—C2—C7—C6−178.74 (13)O1—C14—C15—O2−0.6 (2)
C3—C2—C7—C60.7 (2)C13—C14—C15—O2177.66 (12)
N3—C2—C7—C8−0.15 (16)O1—C14—C15—C16−177.82 (12)
C3—C2—C7—C8179.24 (13)C13—C14—C15—C160.4 (2)
C6—C7—C8—C9178.27 (16)O2—C15—C16—O31.6 (2)
C2—C7—C8—C9−0.04 (16)C14—C15—C16—O3178.93 (12)
C7—C8—C9—N30.22 (16)O2—C15—C16—C17−177.94 (12)
C7—C8—C9—C10−177.98 (14)C14—C15—C16—C17−0.6 (2)
C2—N3—C9—C8−0.32 (16)O3—C16—C17—C12−178.85 (12)
C1—N3—C9—C8−179.42 (13)C15—C16—C17—C120.7 (2)
C2—N3—C9—C10178.06 (12)C13—C12—C17—C16−0.6 (2)
C1—N3—C9—C10−1.0 (2)C11—C12—C17—C16177.82 (13)
N1—N2—C10—C9179.93 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2O···O4i0.841.802.6119 (14)164
O1—H1O···N2i0.842.062.7759 (15)142
O3—H3O···O2ii0.842.122.8469 (14)144
O1—H1O···O20.842.512.8570 (14)106
O3—H3O···O20.842.312.7560 (14)113

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+2, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2532).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA..
  • Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008a). Acta Cryst. E64, o2108. [PMC free article] [PubMed]
  • Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008b). Acta Cryst. E64, o2481. [PMC free article] [PubMed]
  • Khaledi, H., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o169. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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