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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Sep 3;67(Pt 10):o2547. doi: 10.1107/S1600536811035070

4-Dimethyl­amino-N′-(2-hy­droxy-3,5-diiodo­benzyl­idene)benzohydrazide

Fu-Lin Mao a,b,*, Wen-Sheng Li a, Xiao-Ping Zhou a,*
PMCID: PMC3201515  PMID: 22058727

Abstract

The title mol­ecule, C16H15I2N3O2, adopts an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 6.4 (2)°. An intra­molecular O—H⋯N hydrogen bond occurs. In the crystal, mol­ecules are linked through inter­molecular N—H⋯O hydrogen bonds, forming chains propagating in the c-axis direction.

Related literature

For medical applications of hydrazones, see: Ajani et al. (2010 ▶); Zhang et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Su et al. (2011a ▶,b ▶); Khaledi et al. (2010 ▶); Zhou & Yang (2010 ▶); Ji & Lu (2010 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶). For similar compounds that we have reported recently, see: Dai & Mao (2010a ▶,b ▶).graphic file with name e-67-o2547-scheme1.jpg

Experimental

Crystal data

  • C16H15I2N3O2

  • M r = 535.11

  • Monoclinic, Inline graphic

  • a = 20.387 (4) Å

  • b = 9.0000 (16) Å

  • c = 9.8355 (17) Å

  • β = 94.320 (2)°

  • V = 1799.5 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.51 mm−1

  • T = 298 K

  • 0.17 × 0.17 × 0.15 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.587, T max = 0.621

  • 9471 measured reflections

  • 3892 independent reflections

  • 2551 reflections with I > 2σ(I)

  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042

  • wR(F 2) = 0.094

  • S = 1.04

  • 3892 reflections

  • 214 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.70 e Å−3

  • Δρmin = −1.06 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035070/su2309sup1.cif

e-67-o2547-sup1.cif (16.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035070/su2309Isup2.hkl

e-67-o2547-Isup2.hkl (190.8KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811035070/su2309Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1 0.82 1.91 2.623 (5) 144
N2—H2⋯O2i 0.90 (1) 2.16 (2) 3.016 (5) 159 (5)
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Symmetry code: (i) Inline graphic.

Acknowledgments

We are grateful to the Jiangsu Provincial Key Laboratory of Coastal Wetland Bioresources and Environmental Protection for financial support (project No. JLCBE07026).

supplementary crystallographic information

Comment

In the last few years, medical applications of a number of hydrazone compounds have received considerable attention (Ajani et al., 2010; Zhang et al., 2010; Angelusiu et al., 2010). The structures of several hydrazone derivatives have also been determined (Su et al., 2011a,b; Khaledi et al., 2010; Zhou & Yang, 2010; Ji & Lu, 2010; Singh & Singh, 2010; Ahmad et al., 2010). As a continuation of our work in this area (Dai & Mao, 2010a,b), we report herein on the structure of the new title hydrazone compound.

In the molecule of the title compound, there is an intramolecular O—H···N hydrogen bond, as shown in Fig. 1. The dihedral angle between the (C1-C6) and (C9-C14) benzene rings is 6.4 (2)°. The bond lengths and angles are comparable to those found in the hydrazone compounds cited above.

In the crystal, the hydrazone molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), to form one-dimensional chains in the c direction (Fig. 2).

Experimental

The reaction of 2-hydroxy-3,5-diiodobenzaldehyde (0.374 g, 1 mmol) with 4-dimethylaminobenzohydrazide (0.179 g, 1 mmol) in 50 ml methanol at room temperature afforded the title compound. Colorless block-shaped single crystals were formed by slow evaporation of the clear solution in air.

Refinement

The H2 atom was located in a difference Fourier map and refined with a distance restraint, N—H = 0.90 (1) Å, and Uiso = 0.08 Å2. The other H-atoms were positioned geometrically and refined as riding: O—H = 0.82 Å, C—H = 0.93 and 0.96 Å, for CH and CH3 H-atoms, respectively, with Uiso(H) = k × Ueq(O,C), where k = 1.5 for OH and CH3 H-atoms and k = 1.2 for all other H-atoms.

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title molecule, showing 30% probability displacement ellipsoids and the atomic numbering. The intramolecular N-H···O hydrogen bond is shown as a dashed line (See Table 1 for details).

Fig. 2.

Fig. 2.

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Crystal packing of the title compound, viewed down the b axis, with the O-H···N and N-H···O hydrogen bonds shown as dashed lines (see Table 1 for details).

Crystal data

C16H15I2N3O2 F(000) = 1016
Mr = 535.11 Dx = 1.975 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 2040 reflections
a = 20.387 (4) Å θ = 2.4–24.5°
b = 9.0000 (16) Å µ = 3.51 mm−1
c = 9.8355 (17) Å T = 298 K
β = 94.320 (2)° Block, colourless
V = 1799.5 (5) Å3 0.17 × 0.17 × 0.15 mm
Z = 4
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Data collection

Bruker SMART CCD area-detector diffractometer 3892 independent reflections
Radiation source: fine-focus sealed tube 2551 reflections with I > 2σ(I)
graphite Rint = 0.033
ω scans θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001) h = −25→18
Tmin = 0.587, Tmax = 0.621 k = −11→11
9471 measured reflections l = −12→12
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094 H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.036P)2 + 0.0912P] where P = (Fo2 + 2Fc2)/3
3892 reflections (Δ/σ)max < 0.001
214 parameters Δρmax = 0.70 e Å−3
1 restraint Δρmin = −1.06 e Å−3
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Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
I1 0.430896 (19) 0.68628 (4) 0.37673 (4) 0.06296 (15)
I2 0.41396 (2) 0.29856 (5) −0.12108 (4) 0.07864 (18)
N1 0.17425 (19) 0.6984 (4) 0.1129 (4) 0.0460 (10)
N2 0.1097 (2) 0.7279 (5) 0.0734 (4) 0.0486 (11)
N3 −0.1967 (2) 0.8856 (6) −0.0186 (5) 0.0745 (15)
O1 0.28501 (17) 0.7467 (4) 0.2597 (3) 0.0556 (9)
H1 0.2449 0.7485 0.2442 0.083*
O2 0.09491 (16) 0.8441 (4) 0.2731 (3) 0.0528 (9)
C1 0.2749 (2) 0.5829 (5) 0.0659 (4) 0.0411 (12)
C2 0.3110 (2) 0.6455 (5) 0.1782 (5) 0.0423 (12)
C3 0.3763 (2) 0.6018 (5) 0.2055 (5) 0.0400 (11)
C4 0.4057 (2) 0.5002 (5) 0.1236 (4) 0.0407 (11)
H4 0.4491 0.4712 0.1439 0.049*
C5 0.3697 (2) 0.4431 (5) 0.0118 (5) 0.0408 (11)
C6 0.3058 (2) 0.4842 (5) −0.0169 (5) 0.0459 (12)
H6 0.2824 0.4452 −0.0936 0.055*
C7 0.2062 (2) 0.6198 (6) 0.0322 (5) 0.0481 (13)
H7 0.1853 0.5858 −0.0492 0.058*
C8 0.0719 (2) 0.8033 (5) 0.1611 (5) 0.0427 (12)
C9 0.0026 (2) 0.8230 (5) 0.1103 (5) 0.0406 (11)
C10 −0.0353 (2) 0.9280 (5) 0.1713 (5) 0.0457 (13)
H10 −0.0161 0.9855 0.2423 0.055*
C11 −0.1005 (2) 0.9493 (6) 0.1295 (5) 0.0480 (13)
H11 −0.1245 1.0206 0.1731 0.058*
C12 −0.1311 (2) 0.8675 (6) 0.0245 (5) 0.0500 (13)
C13 −0.0930 (3) 0.7631 (7) −0.0376 (6) 0.0675 (17)
H13 −0.1121 0.7059 −0.1088 0.081*
C14 −0.0279 (3) 0.7425 (6) 0.0035 (5) 0.0563 (14)
H14 −0.0037 0.6728 −0.0414 0.068*
C15 −0.2392 (3) 0.9775 (7) 0.0537 (6) 0.0759 (19)
H15A −0.2365 0.9488 0.1480 0.114*
H15B −0.2837 0.9659 0.0155 0.114*
H15C −0.2261 1.0794 0.0464 0.114*
C16 −0.2223 (3) 0.8274 (7) −0.1472 (6) 0.083 (2)
H16A −0.1876 0.8203 −0.2076 0.124*
H16B −0.2561 0.8922 −0.1862 0.124*
H16C −0.2405 0.7305 −0.1341 0.124*
H2 0.095 (3) 0.714 (6) −0.014 (2) 0.080*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
I1 0.0550 (3) 0.0776 (3) 0.0542 (3) −0.0025 (2) −0.00991 (18) −0.02124 (19)
I2 0.0613 (3) 0.0960 (4) 0.0767 (3) 0.0256 (2) −0.0072 (2) −0.0429 (2)
N1 0.034 (2) 0.068 (3) 0.036 (2) 0.010 (2) 0.0000 (18) 0.004 (2)
N2 0.036 (2) 0.075 (3) 0.034 (2) 0.015 (2) 0.0013 (19) 0.003 (2)
N3 0.041 (3) 0.121 (4) 0.060 (3) 0.024 (3) −0.007 (2) −0.013 (3)
O1 0.049 (2) 0.071 (2) 0.046 (2) 0.011 (2) 0.0005 (19) −0.0170 (18)
O2 0.044 (2) 0.083 (3) 0.0309 (19) 0.0048 (18) −0.0020 (16) −0.0016 (18)
C1 0.040 (3) 0.055 (3) 0.028 (3) 0.004 (2) 0.000 (2) 0.002 (2)
C2 0.051 (3) 0.045 (3) 0.032 (3) 0.002 (2) 0.006 (2) −0.002 (2)
C3 0.036 (3) 0.047 (3) 0.036 (3) −0.003 (2) −0.004 (2) −0.003 (2)
C4 0.034 (3) 0.045 (3) 0.042 (3) 0.006 (2) −0.003 (2) 0.007 (2)
C5 0.041 (3) 0.046 (3) 0.036 (3) 0.007 (2) 0.004 (2) −0.004 (2)
C6 0.049 (3) 0.054 (3) 0.034 (3) −0.002 (3) −0.003 (2) −0.009 (2)
C7 0.040 (3) 0.065 (3) 0.038 (3) 0.004 (3) −0.006 (2) 0.002 (3)
C8 0.044 (3) 0.050 (3) 0.035 (3) 0.007 (2) 0.007 (2) 0.011 (2)
C9 0.036 (3) 0.051 (3) 0.034 (3) 0.006 (2) 0.002 (2) 0.005 (2)
C10 0.043 (3) 0.057 (3) 0.036 (3) 0.004 (3) −0.002 (2) −0.004 (2)
C11 0.050 (3) 0.056 (3) 0.039 (3) 0.014 (3) 0.008 (2) −0.001 (2)
C12 0.037 (3) 0.068 (4) 0.045 (3) 0.008 (3) 0.004 (2) 0.006 (3)
C13 0.051 (4) 0.099 (5) 0.051 (4) 0.008 (3) −0.008 (3) −0.025 (3)
C14 0.040 (3) 0.074 (4) 0.054 (3) 0.012 (3) 0.000 (3) −0.022 (3)
C15 0.043 (3) 0.099 (5) 0.085 (5) 0.023 (3) 0.004 (3) 0.008 (4)
C16 0.046 (4) 0.139 (6) 0.060 (4) −0.001 (4) −0.014 (3) 0.001 (4)
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Geometric parameters (Å, °)

I1—C3 2.091 (4) C6—H6 0.9300
I2—C5 2.096 (4) C7—H7 0.9300
N1—C7 1.278 (6) C8—C9 1.474 (6)
N1—N2 1.371 (5) C9—C14 1.385 (6)
N2—C8 1.378 (6) C9—C10 1.385 (6)
N2—H2 0.898 (10) C10—C11 1.375 (6)
N3—C12 1.380 (6) C10—H10 0.9300
N3—C15 1.427 (7) C11—C12 1.380 (7)
N3—C16 1.431 (7) C11—H11 0.9300
O1—C2 1.348 (5) C12—C13 1.390 (7)
O1—H1 0.8200 C13—C14 1.370 (7)
O2—C8 1.221 (5) C13—H13 0.9300
C1—C6 1.389 (6) C14—H14 0.9300
C1—C2 1.400 (6) C15—H15A 0.9600
C1—C7 1.452 (6) C15—H15B 0.9600
C2—C3 1.393 (6) C15—H15C 0.9600
C3—C4 1.385 (6) C16—H16A 0.9600
C4—C5 1.375 (6) C16—H16B 0.9600
C4—H4 0.9300 C16—H16C 0.9600
C5—C6 1.363 (6)
C7—N1—N2 117.1 (4) N2—C8—C9 114.4 (4)
N1—N2—C8 119.2 (4) C14—C9—C10 117.0 (4)
N1—N2—H2 120 (4) C14—C9—C8 123.9 (4)
C8—N2—H2 120 (4) C10—C9—C8 119.1 (4)
C12—N3—C15 121.7 (5) C11—C10—C9 121.5 (5)
C12—N3—C16 120.6 (5) C11—C10—H10 119.2
C15—N3—C16 117.2 (5) C9—C10—H10 119.2
C2—O1—H1 109.5 C10—C11—C12 121.5 (5)
C6—C1—C2 119.0 (4) C10—C11—H11 119.2
C6—C1—C7 119.0 (4) C12—C11—H11 119.2
C2—C1—C7 122.0 (4) C11—C12—N3 122.7 (5)
O1—C2—C3 119.3 (4) C11—C12—C13 117.0 (5)
O1—C2—C1 122.3 (4) N3—C12—C13 120.3 (5)
C3—C2—C1 118.5 (4) C14—C13—C12 121.5 (5)
C4—C3—C2 121.6 (4) C14—C13—H13 119.2
C4—C3—I1 118.7 (3) C12—C13—H13 119.2
C2—C3—I1 119.7 (3) C13—C14—C9 121.5 (5)
C5—C4—C3 118.9 (4) C13—C14—H14 119.3
C5—C4—H4 120.6 C9—C14—H14 119.3
C3—C4—H4 120.6 N3—C15—H15A 109.5
C6—C5—C4 120.6 (4) N3—C15—H15B 109.5
C6—C5—I2 119.2 (3) H15A—C15—H15B 109.5
C4—C5—I2 120.1 (3) N3—C15—H15C 109.5
C5—C6—C1 121.4 (4) H15A—C15—H15C 109.5
C5—C6—H6 119.3 H15B—C15—H15C 109.5
C1—C6—H6 119.3 N3—C16—H16A 109.5
N1—C7—C1 120.8 (4) N3—C16—H16B 109.5
N1—C7—H7 119.6 H16A—C16—H16B 109.5
C1—C7—H7 119.6 N3—C16—H16C 109.5
O2—C8—N2 121.2 (4) H16A—C16—H16C 109.5
O2—C8—C9 124.3 (4) H16B—C16—H16C 109.5
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O1—H1···N1 0.82 1.91 2.623 (5) 144.
N2—H2···O2i 0.90 (1) 2.16 (2) 3.016 (5) 159 (5)
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Symmetry codes: (i) x, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2309).

References

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  4. Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035070/su2309sup1.cif

e-67-o2547-sup1.cif (16.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035070/su2309Isup2.hkl

e-67-o2547-Isup2.hkl (190.8KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811035070/su2309Isup3.cml

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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