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Acta Cryst. (2008). E64, o1777    [ doi:10.1107/S1600536808026044 ]

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

S. Puvaneswary, H. M. Ali, W. T. Robinson and S. W. Ng

Abstract top

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.

Comment top

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.

Related literature top

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

Experimental top

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 top

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).

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 of (I) (Barbour, 2001) at the 50% probability level. Dashed line indicates H-bonding.
N'-(2-Hydroxy-5-nitrobenzylidene)-2-(1H-indol-3-yl)acetohydrazide top
Crystal data top
C17H14N4O4F000 = 1408
Mr = 338.32Dx = 1.404 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		2059 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 top
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 Å−3
3679 reflectionsΔρmin = −0.21 e Å−3
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
Crystal data top
C17H14N4O4V = 3202.0 (1) Å3
Mr = 338.32Z = 8
Orthorhombic, PbcaMo Kα
a = 9.5387 (2) ŵ = 0.10 mm−1
b = 11.2724 (3) ÅT = 100 (2) K
c = 29.7796 (7) Å0.30 × 0.25 × 0.20 mm
Data collection top
Bruker SMART APEX
diffractometer		3679 independent reflections
Absorption correction: None2059 reflections with I > 2σ(I)
47721 measured reflectionsRint = 0.053
Refinement top
R[F2 > 2σ(F2)] = 0.044228 parameters
wR(F2) = 0.160H-atom parameters constrained
S = 1.02Δρmax = 0.18 e Å−3
3679 reflectionsΔρmin = −0.21 e Å−3
Special details top

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) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···N20.841.852.583 (2)146
N3—H3n···O4i0.882.072.827 (2)144
Symmetry codes: (i) x−1/2, y, −z+3/2.
Acknowledgements top

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.

references
References top

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.

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