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

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

doi:10.1107/S1600536808026044

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1777

doi:10.1107/S1600536808026044

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

Subramaniam Puvaneswary,^a Hapipah M. Ali,^a Ward T. Robinson ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 10 July 2008; accepted 12 August 2008; online 16 August 2008)

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 ); Martin Zarza et al. (1989 ).

Experimental

Crystal data

C₁₇H₁₄N₄O₄
M_r = 338.32
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.160
S = 1.02
3679 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N2	0.84	1.85	2.583 (2)	146
N3—H3n⋯O4ⁱ	0.88	2.07	2.827 (2)	144
Symmetry code: (i) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: 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

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

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

checkCIF report

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.

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

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

C₁₇H₁₄N₄O₄	F(000) = 1408
M_r = 338.32	D_x = 1.404 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3679 reflections
a = 9.5387 (2) Å	θ = 2.5–22.2°
b = 11.2724 (3) Å	µ = 0.10 mm⁻¹
c = 29.7796 (7) Å	T = 100 K
V = 3202.0 (1) Å³	Irregular block, yellow
Z = 8	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	2059 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.053
Graphite monochromator	θ_max = 27.5°, θ_min = 1.4°
ω scans	h = −12→12
47721 measured reflections	k = −14→13
3679 independent reflections	l = −38→38

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.160	w = 1/[σ²(F_o²) + (0.0885P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3679 reflections	Δρ_max = 0.18 e Å⁻³
228 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.007 (1)

Crystal data top

C₁₇H₁₄N₄O₄	V = 3202.0 (1) Å³
M_r = 338.32	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.5387 (2) Å	µ = 0.10 mm⁻¹
b = 11.2724 (3) Å	T = 100 K
c = 29.7796 (7) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	2059 reflections with I > 2σ(I)
47721 measured reflections	R_int = 0.053
3679 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.02	Δρ_max = 0.18 e Å⁻³
3679 reflections	Δρ_min = −0.21 e Å⁻³
228 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.76143 (16)	0.34962 (15)	0.66810 (5)	0.0747 (5)
H1O	0.7344	0.4058	0.6845	0.112*
O2	0.50825 (18)	0.27110 (16)	0.47819 (5)	0.0896 (6)
O3	0.36688 (19)	0.40496 (16)	0.50246 (5)	0.0853 (5)
O4	0.78329 (15)	0.61201 (15)	0.75230 (5)	0.0790 (5)
N1	0.4670 (2)	0.33901 (17)	0.50757 (6)	0.0647 (5)
N2	0.60812 (15)	0.52866 (14)	0.69094 (5)	0.0522 (4)
N3	0.56843 (16)	0.61209 (15)	0.72184 (5)	0.0543 (5)
H3N	0.4821	0.6397	0.7223	0.065*
N4	0.79603 (19)	0.75966 (17)	0.89103 (6)	0.0712 (5)
H4N	0.8598	0.7879	0.9095	0.085*
C1	0.6858 (2)	0.34823 (18)	0.63004 (7)	0.0563 (5)
C2	0.7229 (2)	0.26733 (18)	0.59698 (8)	0.0651 (6)
H2	0.7980	0.2137	0.6022	0.078*
C3	0.6523 (2)	0.26386 (18)	0.55689 (7)	0.0625 (6)
H3	0.6787	0.2090	0.5342	0.075*
C4	0.5426 (2)	0.34134 (17)	0.55005 (6)	0.0538 (5)
C5	0.5011 (2)	0.42048 (16)	0.58253 (6)	0.0511 (5)
H5	0.4237	0.4715	0.5772	0.061*
C6	0.57211 (19)	0.42584 (16)	0.62300 (6)	0.0473 (5)
C7	0.53086 (19)	0.51242 (17)	0.65658 (6)	0.0505 (5)
H7	0.4468	0.5567	0.6530	0.061*
C8	0.6644 (2)	0.65087 (18)	0.75150 (6)	0.0555 (5)
C9	0.6133 (2)	0.7485 (2)	0.78219 (6)	0.0643 (6)
H9A	0.6427	0.8262	0.7699	0.077*
H9B	0.5095	0.7472	0.7832	0.077*
C10	0.6695 (2)	0.73543 (17)	0.82885 (6)	0.0546 (5)
C11	0.7735 (2)	0.7979 (2)	0.84821 (7)	0.0684 (6)
H11	0.8242	0.8600	0.8340	0.082*
C12	0.62245 (19)	0.65262 (16)	0.86168 (7)	0.0514 (5)
C13	0.5173 (2)	0.56695 (18)	0.86298 (8)	0.0626 (6)
H13	0.4599	0.5530	0.8374	0.075*
C14	0.4978 (3)	0.50326 (19)	0.90151 (9)	0.0745 (7)
H14	0.4262	0.4447	0.9024	0.089*
C15	0.5803 (3)	0.5221 (2)	0.93952 (8)	0.0753 (7)
H15	0.5640	0.4760	0.9657	0.090*
C16	0.6847 (2)	0.6062 (2)	0.93974 (7)	0.0667 (6)
H16	0.7411	0.6194	0.9655	0.080*
C17	0.7037 (2)	0.67047 (18)	0.90073 (7)	0.0561 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0634 (10)	0.0901 (11)	0.0707 (10)	0.0201 (8)	−0.0089 (8)	0.0030 (8)
O2	0.0991 (14)	0.1023 (13)	0.0672 (11)	−0.0122 (10)	0.0139 (9)	−0.0333 (10)
O3	0.0835 (12)	0.0954 (12)	0.0771 (11)	0.0045 (10)	−0.0245 (9)	−0.0215 (9)
O4	0.0393 (9)	0.1232 (13)	0.0745 (11)	0.0156 (8)	−0.0106 (7)	−0.0360 (9)
N1	0.0663 (12)	0.0712 (12)	0.0566 (11)	−0.0201 (10)	0.0062 (9)	−0.0134 (10)
N2	0.0406 (9)	0.0683 (10)	0.0477 (9)	−0.0033 (8)	0.0012 (7)	−0.0058 (8)
N3	0.0360 (8)	0.0762 (11)	0.0507 (10)	0.0042 (8)	0.0002 (7)	−0.0134 (8)
N4	0.0664 (12)	0.0860 (13)	0.0612 (11)	−0.0182 (10)	−0.0085 (9)	−0.0171 (10)
C1	0.0460 (11)	0.0607 (12)	0.0623 (13)	−0.0011 (9)	0.0046 (10)	0.0044 (10)
C2	0.0548 (13)	0.0590 (13)	0.0814 (16)	0.0065 (10)	0.0103 (12)	0.0004 (11)
C3	0.0592 (14)	0.0557 (12)	0.0724 (15)	−0.0079 (10)	0.0201 (12)	−0.0112 (10)
C4	0.0512 (12)	0.0533 (11)	0.0568 (12)	−0.0139 (9)	0.0058 (10)	−0.0048 (9)
C5	0.0460 (11)	0.0536 (11)	0.0536 (11)	−0.0039 (9)	0.0030 (8)	−0.0029 (9)
C6	0.0409 (10)	0.0498 (10)	0.0513 (11)	−0.0052 (8)	0.0050 (8)	0.0011 (9)
C7	0.0416 (11)	0.0583 (11)	0.0515 (11)	−0.0014 (9)	0.0018 (9)	−0.0006 (9)
C8	0.0428 (12)	0.0750 (13)	0.0488 (11)	0.0012 (10)	−0.0009 (9)	−0.0068 (10)
C9	0.0573 (13)	0.0742 (14)	0.0613 (13)	0.0078 (11)	−0.0020 (10)	−0.0119 (11)
C10	0.0496 (12)	0.0617 (12)	0.0524 (11)	−0.0006 (9)	0.0004 (9)	−0.0154 (9)
C11	0.0671 (15)	0.0730 (14)	0.0650 (14)	−0.0150 (12)	0.0039 (11)	−0.0092 (11)
C12	0.0443 (11)	0.0532 (11)	0.0568 (12)	0.0047 (9)	0.0009 (9)	−0.0189 (9)
C13	0.0534 (13)	0.0564 (12)	0.0781 (15)	−0.0004 (10)	−0.0012 (11)	−0.0154 (11)
C14	0.0665 (15)	0.0541 (12)	0.103 (2)	−0.0025 (11)	0.0122 (14)	−0.0064 (13)
C15	0.0858 (18)	0.0594 (13)	0.0808 (17)	0.0180 (13)	0.0207 (14)	0.0039 (12)
C16	0.0717 (15)	0.0718 (14)	0.0566 (13)	0.0192 (13)	−0.0007 (11)	−0.0090 (11)
C17	0.0523 (12)	0.0578 (12)	0.0583 (12)	0.0059 (10)	0.0013 (10)	−0.0171 (10)

Geometric parameters (Å, º) top

O1—C1	1.344 (2)	C5—H5	0.9500
O1—H1O	0.8400	C6—C7	1.452 (3)
O2—N1	1.227 (2)	C7—H7	0.9500
O3—N1	1.220 (2)	C8—C9	1.512 (3)
O4—C8	1.216 (2)	C9—C10	1.497 (3)
N1—C4	1.456 (3)	C9—H9A	0.9900
N2—C7	1.274 (2)	C9—H9B	0.9900
N2—N3	1.369 (2)	C10—C11	1.347 (3)
N3—C8	1.345 (2)	C10—C12	1.424 (3)
N3—H3N	0.8800	C11—H11	0.9500
N4—C11	1.363 (3)	C12—C13	1.393 (3)
N4—C17	1.367 (3)	C12—C17	1.412 (3)
N4—H4N	0.8800	C13—C14	1.366 (3)
C1—C2	1.388 (3)	C13—H13	0.9500
C1—C6	1.409 (3)	C14—C15	1.395 (3)
C2—C3	1.371 (3)	C14—H14	0.9500
C2—H2	0.9500	C15—C16	1.375 (3)
C3—C4	1.378 (3)	C15—H15	0.9500
C3—H3	0.9500	C16—C17	1.381 (3)
C4—C5	1.374 (3)	C16—H16	0.9500
C5—C6	1.384 (3)

C1—O1—H1O	109.5	O4—C8—C9	123.48 (18)
O3—N1—O2	122.85 (19)	N3—C8—C9	114.46 (18)
O3—N1—C4	119.01 (18)	C10—C9—C8	111.95 (17)
O2—N1—C4	118.1 (2)	C10—C9—H9A	109.2
C7—N2—N3	118.59 (16)	C8—C9—H9A	109.2
C8—N3—N2	118.45 (16)	C10—C9—H9B	109.2
C8—N3—H3N	120.8	C8—C9—H9B	109.2
N2—N3—H3N	120.8	H9A—C9—H9B	107.9
C11—N4—C17	109.21 (17)	C11—C10—C12	106.33 (18)
C11—N4—H4N	125.4	C11—C10—C9	127.6 (2)
C17—N4—H4N	125.4	C12—C10—C9	126.11 (18)
O1—C1—C2	117.97 (19)	C10—C11—N4	110.5 (2)
O1—C1—C6	122.12 (18)	C10—C11—H11	124.7
C2—C1—C6	119.91 (19)	N4—C11—H11	124.7
C3—C2—C1	120.8 (2)	C13—C12—C17	118.12 (19)
C3—C2—H2	119.6	C13—C12—C10	134.45 (19)
C1—C2—H2	119.6	C17—C12—C10	107.40 (17)
C2—C3—C4	118.89 (19)	C14—C13—C12	119.1 (2)
C2—C3—H3	120.6	C14—C13—H13	120.5
C4—C3—H3	120.6	C12—C13—H13	120.5
C5—C4—C3	121.73 (19)	C13—C14—C15	121.7 (2)
C5—C4—N1	118.73 (19)	C13—C14—H14	119.2
C3—C4—N1	119.54 (18)	C15—C14—H14	119.2
C4—C5—C6	120.04 (18)	C16—C15—C14	121.2 (2)
C4—C5—H5	120.0	C16—C15—H15	119.4
C6—C5—H5	120.0	C14—C15—H15	119.4
C5—C6—C1	118.63 (17)	C15—C16—C17	116.9 (2)
C5—C6—C7	119.78 (17)	C15—C16—H16	121.5
C1—C6—C7	121.58 (18)	C17—C16—H16	121.5
N2—C7—C6	119.53 (17)	N4—C17—C16	130.4 (2)
N2—C7—H7	120.2	N4—C17—C12	106.52 (18)
C6—C7—H7	120.2	C16—C17—C12	123.1 (2)
O4—C8—N3	122.03 (18)

C7—N2—N3—C8	−163.35 (18)	N3—C8—C9—C10	142.14 (19)
O1—C1—C2—C3	−178.10 (19)	C8—C9—C10—C11	103.7 (2)
C6—C1—C2—C3	1.7 (3)	C8—C9—C10—C12	−76.0 (3)
C1—C2—C3—C4	−0.7 (3)	C12—C10—C11—N4	0.4 (2)
C2—C3—C4—C5	−0.9 (3)	C9—C10—C11—N4	−179.39 (19)
C2—C3—C4—N1	179.78 (17)	C17—N4—C11—C10	−0.8 (2)
O3—N1—C4—C5	−1.9 (3)	C11—C10—C12—C13	177.9 (2)
O2—N1—C4—C5	177.32 (17)	C9—C10—C12—C13	−2.4 (3)
O3—N1—C4—C3	177.38 (18)	C11—C10—C12—C17	0.1 (2)
O2—N1—C4—C3	−3.4 (3)	C9—C10—C12—C17	179.90 (18)
C3—C4—C5—C6	1.6 (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—C15	0.1 (3)
C4—C5—C6—C7	177.88 (16)	C13—C14—C15—C16	0.2 (3)
O1—C1—C6—C5	178.74 (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—C7	0.3 (3)	C11—N4—C17—C12	0.8 (2)
C2—C1—C6—C7	−179.43 (17)	C15—C16—C17—N4	179.0 (2)
N3—N2—C7—C6	178.97 (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—N2	8.3 (3)	C10—C12—C17—N4	−0.6 (2)
N2—N3—C8—O4	−1.8 (3)	C13—C12—C17—C16	0.8 (3)
N2—N3—C8—C9	176.17 (17)	C10—C12—C17—C16	178.93 (18)
O4—C8—C9—C10	−39.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N2	0.84	1.85	2.583 (2)	146
N3—H3n···O4ⁱ	0.88	2.07	2.827 (2)	144
N4—H4n···O2ⁱⁱ	0.88	2.49	3.216 (2)	140

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₄O₄
M_r	338.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	9.5387 (2), 11.2724 (3), 29.7796 (7)
V (Å³)	3202.0 (1)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	47721, 3679, 2059
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.160, 1.02
No. of reflections	3679
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N2	0.84	1.85	2.583 (2)	146
N3—H3n···O4ⁱ	0.88	2.07	2.827 (2)	144

Symmetry code: (i) x−1/2, y, −z+3/2.

Acknowledgements

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.

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