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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1777.
Published online 2008 August 16. doi:  10.1107/S1600536808026044
PMCID: PMC2960495

N′-(2-Hydr­oxy-5-nitro­benzyl­idene)-2-(1H-indol-3-yl)acetohydrazide

Abstract

The mol­ecule of the title compound, C17H14N4O4, uses its amide –NH– group to form a hydrogen bond to the amido –C(=O)– group of an adjacent mol­ecule to furnish a linear chain structure. The hydr­oxy group forms an intra­molecular hydrogen bond; the indolyl –NH– unit does not engage in any strong hydrogen-bonding inter­actions.

Related literature

For similar compounds, see: Martin Reyes et al. (1986 [triangle]); Martin Zarza et al. (1989 [triangle]).

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Object name is e-64-o1777-scheme1.jpg

Experimental

Crystal data

  • C17H14N4O4
  • M r = 338.32
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1777-efi1.jpg
  • a = 9.5387 (2) Å
  • b = 11.2724 (3) Å
  • c = 29.7796 (7) Å
  • V = 3202.0 (1) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 (2) K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 47721 measured reflections
  • 3679 independent reflections
  • 2059 reflections with I > 2σ(I)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.160
  • S = 1.02
  • 3679 reflections
  • 228 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; 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, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026044/bq2091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026044/bq2091Isup2.hkl

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

Acknowledgments

We thank the Science Fund (12–02-03–2031, 12–02-03–2051) and the University of Malaya (PJP) for supporting this study. We are grateful to the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

There are many examples of Schiff bases derived from the condensation of salicylaldehyde and substituted salicyldehydes with hydrazides such as the ones reported by Martin Reyes et al. (1986) and Martin Zarza et al. (1989). The title compound (Fig. 1) is another example. The molecule uses its amido –NH– group to form a hydrogen bond to the amido –C(=O)– group of an adjacent molecule to furnish a linear chain structure.

Experimental

The Schiff base was prepared by refluxing a solution of indole-3-acetic acid hydrazide (0.34 g, 1.80 mmol) and 5-nitrosalicylaldehyde (0.30 g, 1.80 mmol) in acidified ethanol (25 ml) for 2 h. On cooling to room temperature, yellow crystals separated out.

Refinement

All H-atoms were placed in calculated positions (C—H 0.95, N—H 0.88, O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5Ueq(C,N,O).

Figures

Fig. 1.
Thermal ellipsoid plot of (I) (Barbour, 2001) at the 50% probability level. Dashed line indicates H-bonding.

Crystal data

C17H14N4O4F000 = 1408
Mr = 338.32Dx = 1.404 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3679 reflections
a = 9.5387 (2) Åθ = 2.5–22.2º
b = 11.2724 (3) ŵ = 0.10 mm1
c = 29.7796 (7) ÅT = 100 (2) K
V = 3202.0 (1) Å3Irregular block, yellow
Z = 80.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer2059 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
Monochromator: graphiteθmax = 27.5º
T = 100(2) Kθmin = 1.4º
ω scansh = −12→12
Absorption correction: Nonek = −14→13
47721 measured reflectionsl = −38→38
3679 independent reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044  w = 1/[σ2(Fo2) + (0.0885P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.160(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.18 e Å3
3679 reflectionsΔρmin = −0.21 e Å3
228 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.007 (1)
Secondary atom site location: difference Fourier map

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.

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

xyzUiso*/Ueq
O10.76143 (16)0.34962 (15)0.66810 (5)0.0747 (5)
H1O0.73440.40580.68450.112*
O20.50825 (18)0.27110 (16)0.47819 (5)0.0896 (6)
O30.36688 (19)0.40496 (16)0.50246 (5)0.0853 (5)
O40.78329 (15)0.61201 (15)0.75230 (5)0.0790 (5)
N10.4670 (2)0.33901 (17)0.50757 (6)0.0647 (5)
N20.60812 (15)0.52866 (14)0.69094 (5)0.0522 (4)
N30.56843 (16)0.61209 (15)0.72184 (5)0.0543 (5)
H3N0.48210.63970.72230.065*
N40.79603 (19)0.75966 (17)0.89103 (6)0.0712 (5)
H4N0.85980.78790.90950.085*
C10.6858 (2)0.34823 (18)0.63004 (7)0.0563 (5)
C20.7229 (2)0.26733 (18)0.59698 (8)0.0651 (6)
H20.79800.21370.60220.078*
C30.6523 (2)0.26386 (18)0.55689 (7)0.0625 (6)
H30.67870.20900.53420.075*
C40.5426 (2)0.34134 (17)0.55005 (6)0.0538 (5)
C50.5011 (2)0.42048 (16)0.58253 (6)0.0511 (5)
H50.42370.47150.57720.061*
C60.57211 (19)0.42584 (16)0.62300 (6)0.0473 (5)
C70.53086 (19)0.51242 (17)0.65658 (6)0.0505 (5)
H70.44680.55670.65300.061*
C80.6644 (2)0.65087 (18)0.75150 (6)0.0555 (5)
C90.6133 (2)0.7485 (2)0.78219 (6)0.0643 (6)
H9A0.64270.82620.76990.077*
H9B0.50950.74720.78320.077*
C100.6695 (2)0.73543 (17)0.82885 (6)0.0546 (5)
C110.7735 (2)0.7979 (2)0.84821 (7)0.0684 (6)
H110.82420.86000.83400.082*
C120.62245 (19)0.65262 (16)0.86168 (7)0.0514 (5)
C130.5173 (2)0.56695 (18)0.86298 (8)0.0626 (6)
H130.45990.55300.83740.075*
C140.4978 (3)0.50326 (19)0.90151 (9)0.0745 (7)
H140.42620.44470.90240.089*
C150.5803 (3)0.5221 (2)0.93952 (8)0.0753 (7)
H150.56400.47600.96570.090*
C160.6847 (2)0.6062 (2)0.93974 (7)0.0667 (6)
H160.74110.61940.96550.080*
C170.7037 (2)0.67047 (18)0.90073 (7)0.0561 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0634 (10)0.0901 (11)0.0707 (10)0.0201 (8)−0.0089 (8)0.0030 (8)
O20.0991 (14)0.1023 (13)0.0672 (11)−0.0122 (10)0.0139 (9)−0.0333 (10)
O30.0835 (12)0.0954 (12)0.0771 (11)0.0045 (10)−0.0245 (9)−0.0215 (9)
O40.0393 (9)0.1232 (13)0.0745 (11)0.0156 (8)−0.0106 (7)−0.0360 (9)
N10.0663 (12)0.0712 (12)0.0566 (11)−0.0201 (10)0.0062 (9)−0.0134 (10)
N20.0406 (9)0.0683 (10)0.0477 (9)−0.0033 (8)0.0012 (7)−0.0058 (8)
N30.0360 (8)0.0762 (11)0.0507 (10)0.0042 (8)0.0002 (7)−0.0134 (8)
N40.0664 (12)0.0860 (13)0.0612 (11)−0.0182 (10)−0.0085 (9)−0.0171 (10)
C10.0460 (11)0.0607 (12)0.0623 (13)−0.0011 (9)0.0046 (10)0.0044 (10)
C20.0548 (13)0.0590 (13)0.0814 (16)0.0065 (10)0.0103 (12)0.0004 (11)
C30.0592 (14)0.0557 (12)0.0724 (15)−0.0079 (10)0.0201 (12)−0.0112 (10)
C40.0512 (12)0.0533 (11)0.0568 (12)−0.0139 (9)0.0058 (10)−0.0048 (9)
C50.0460 (11)0.0536 (11)0.0536 (11)−0.0039 (9)0.0030 (8)−0.0029 (9)
C60.0409 (10)0.0498 (10)0.0513 (11)−0.0052 (8)0.0050 (8)0.0011 (9)
C70.0416 (11)0.0583 (11)0.0515 (11)−0.0014 (9)0.0018 (9)−0.0006 (9)
C80.0428 (12)0.0750 (13)0.0488 (11)0.0012 (10)−0.0009 (9)−0.0068 (10)
C90.0573 (13)0.0742 (14)0.0613 (13)0.0078 (11)−0.0020 (10)−0.0119 (11)
C100.0496 (12)0.0617 (12)0.0524 (11)−0.0006 (9)0.0004 (9)−0.0154 (9)
C110.0671 (15)0.0730 (14)0.0650 (14)−0.0150 (12)0.0039 (11)−0.0092 (11)
C120.0443 (11)0.0532 (11)0.0568 (12)0.0047 (9)0.0009 (9)−0.0189 (9)
C130.0534 (13)0.0564 (12)0.0781 (15)−0.0004 (10)−0.0012 (11)−0.0154 (11)
C140.0665 (15)0.0541 (12)0.103 (2)−0.0025 (11)0.0122 (14)−0.0064 (13)
C150.0858 (18)0.0594 (13)0.0808 (17)0.0180 (13)0.0207 (14)0.0039 (12)
C160.0717 (15)0.0718 (14)0.0566 (13)0.0192 (13)−0.0007 (11)−0.0090 (11)
C170.0523 (12)0.0578 (12)0.0583 (12)0.0059 (10)0.0013 (10)−0.0171 (10)

Geometric parameters (Å, °)

O1—C11.344 (2)C5—H50.9500
O1—H1O0.8400C6—C71.452 (3)
O2—N11.227 (2)C7—H70.9500
O3—N11.220 (2)C8—C91.512 (3)
O4—C81.216 (2)C9—C101.497 (3)
N1—C41.456 (3)C9—H9A0.9900
N2—C71.274 (2)C9—H9B0.9900
N2—N31.369 (2)C10—C111.347 (3)
N3—C81.345 (2)C10—C121.424 (3)
N3—H3N0.8800C11—H110.9500
N4—C111.363 (3)C12—C131.393 (3)
N4—C171.367 (3)C12—C171.412 (3)
N4—H4N0.8800C13—C141.366 (3)
C1—C21.388 (3)C13—H130.9500
C1—C61.409 (3)C14—C151.395 (3)
C2—C31.371 (3)C14—H140.9500
C2—H20.9500C15—C161.375 (3)
C3—C41.378 (3)C15—H150.9500
C3—H30.9500C16—C171.381 (3)
C4—C51.374 (3)C16—H160.9500
C5—C61.384 (3)
C1—O1—H1O109.5O4—C8—C9123.48 (18)
O3—N1—O2122.85 (19)N3—C8—C9114.46 (18)
O3—N1—C4119.01 (18)C10—C9—C8111.95 (17)
O2—N1—C4118.1 (2)C10—C9—H9A109.2
C7—N2—N3118.59 (16)C8—C9—H9A109.2
C8—N3—N2118.45 (16)C10—C9—H9B109.2
C8—N3—H3N120.8C8—C9—H9B109.2
N2—N3—H3N120.8H9A—C9—H9B107.9
C11—N4—C17109.21 (17)C11—C10—C12106.33 (18)
C11—N4—H4N125.4C11—C10—C9127.6 (2)
C17—N4—H4N125.4C12—C10—C9126.11 (18)
O1—C1—C2117.97 (19)C10—C11—N4110.5 (2)
O1—C1—C6122.12 (18)C10—C11—H11124.7
C2—C1—C6119.91 (19)N4—C11—H11124.7
C3—C2—C1120.8 (2)C13—C12—C17118.12 (19)
C3—C2—H2119.6C13—C12—C10134.45 (19)
C1—C2—H2119.6C17—C12—C10107.40 (17)
C2—C3—C4118.89 (19)C14—C13—C12119.1 (2)
C2—C3—H3120.6C14—C13—H13120.5
C4—C3—H3120.6C12—C13—H13120.5
C5—C4—C3121.73 (19)C13—C14—C15121.7 (2)
C5—C4—N1118.73 (19)C13—C14—H14119.2
C3—C4—N1119.54 (18)C15—C14—H14119.2
C4—C5—C6120.04 (18)C16—C15—C14121.2 (2)
C4—C5—H5120.0C16—C15—H15119.4
C6—C5—H5120.0C14—C15—H15119.4
C5—C6—C1118.63 (17)C15—C16—C17116.9 (2)
C5—C6—C7119.78 (17)C15—C16—H16121.5
C1—C6—C7121.58 (18)C17—C16—H16121.5
N2—C7—C6119.53 (17)N4—C17—C16130.4 (2)
N2—C7—H7120.2N4—C17—C12106.52 (18)
C6—C7—H7120.2C16—C17—C12123.1 (2)
O4—C8—N3122.03 (18)
C7—N2—N3—C8−163.35 (18)N3—C8—C9—C10142.14 (19)
O1—C1—C2—C3−178.10 (19)C8—C9—C10—C11103.7 (2)
C6—C1—C2—C31.7 (3)C8—C9—C10—C12−76.0 (3)
C1—C2—C3—C4−0.7 (3)C12—C10—C11—N40.4 (2)
C2—C3—C4—C5−0.9 (3)C9—C10—C11—N4−179.39 (19)
C2—C3—C4—N1179.78 (17)C17—N4—C11—C10−0.8 (2)
O3—N1—C4—C5−1.9 (3)C11—C10—C12—C13177.9 (2)
O2—N1—C4—C5177.32 (17)C9—C10—C12—C13−2.4 (3)
O3—N1—C4—C3177.38 (18)C11—C10—C12—C170.1 (2)
O2—N1—C4—C3−3.4 (3)C9—C10—C12—C17179.90 (18)
C3—C4—C5—C61.6 (3)C17—C12—C13—C14−0.6 (3)
N1—C4—C5—C6−179.14 (16)C10—C12—C13—C14−178.1 (2)
C4—C5—C6—C1−0.5 (3)C12—C13—C14—C150.1 (3)
C4—C5—C6—C7177.88 (16)C13—C14—C15—C160.2 (3)
O1—C1—C6—C5178.74 (17)C14—C15—C16—C17−0.1 (3)
C2—C1—C6—C5−1.0 (3)C11—N4—C17—C16−178.7 (2)
O1—C1—C6—C70.3 (3)C11—N4—C17—C120.8 (2)
C2—C1—C6—C7−179.43 (17)C15—C16—C17—N4179.0 (2)
N3—N2—C7—C6178.97 (15)C15—C16—C17—C12−0.4 (3)
C5—C6—C7—N2−170.09 (17)C13—C12—C17—N4−178.75 (16)
C1—C6—C7—N28.3 (3)C10—C12—C17—N4−0.6 (2)
N2—N3—C8—O4−1.8 (3)C13—C12—C17—C160.8 (3)
N2—N3—C8—C9176.17 (17)C10—C12—C17—C16178.93 (18)
O4—C8—C9—C10−39.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1o···N20.841.852.583 (2)146
N3—H3n···O4i0.882.072.827 (2)144
N4—H4n···O2ii0.882.493.216 (2)140

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2091).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Martin Reyes, M. G., Gili, P., Zarza, P. M., Medina Ortega, A. & Diaz Gonzalez, M. C. (1986). Inorg. Chim. Acta, 116, 153–156.
  • Martin Zarza, P., Gili, P., Mederos, A. & Medina, A. (1989). Thermochim. Acta, 156, 231–238.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

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