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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1410.
Published online 2009 May 29. doi:  10.1107/S160053680901914X
PMCID: PMC2969706

N′-(2-Hydr­oxy-3,5-diiodo­benzyl­idene)-2-methoxy­benzohydrazide

Abstract

The title compound, C15H12I2N2O3, was synthesized by the condensation of equimolar amounts of 3,5-diiodo­salicylaldehyde and 2-methoxy­benzohydrazide in a methanol solution. There are two independent mol­ecules, A and B, in the asymmetric unit. The dihedral angle between the two benzene rings is 30.2 (2)° for mol­ecule A and 21.7 (2)° for mol­ecule B. There are intra­molecular O—H(...)N and N—H(...)O hydrogen bonds in each mol­ecule. The crystal studied was an inversion twin with a 0.59 (3):0.41 (3) domain ratio.

Related literature

For background to Schiff bases and their complexes, see: Ali et al. (2005 [triangle]). For related structures, see: Yehye et al. (2008a [triangle],b [triangle]); Jing et al. (2006 [triangle]); Ling et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1410-scheme1.jpg

Experimental

Crystal data

  • C15H12I2N2O3
  • M r = 522.07
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1410-efi1.jpg
  • a = 16.073 (2) Å
  • b = 15.628 (2) Å
  • c = 13.284 (1) Å
  • V = 3336.8 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 3.78 mm−1
  • T = 298 K
  • 0.23 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.432, T max = 0.469
  • 26178 measured reflections
  • 7237 independent reflections
  • 4902 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.101
  • S = 1.00
  • 7237 reflections
  • 407 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.78 e Å−3
  • Δρmin = −0.56 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3436 Friedel pairs
  • Flack parameter: 0.59 (3)

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901914X/sj2624sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901914X/sj2624Isup2.hkl

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

Acknowledgments

We acknowledge Changsha University of Science and Technology for research grants.

supplementary crystallographic information

Comment

Schiff bases such as hydrazides are known to act as versatile ligands in coordination chemistry (Ali et al., 2005). We report herein the crystal structure of the new title benzohydrazide derivative (I), Fig. 1.

Compound (I) consists two independent molecules, A and B in the asymmetric unit. The dihedral angles between the two benzene rings are 30.2 (2)° for A and 21.7 (2)° for B, respectively. All the bond lengths are comparable to those observed in other similar compounds (Yehye et al., 2008a,b; Jing et al., 2006); Ling et al., 2008). There are two intramolecular O–H···N and N–H···O hydrogen bonds (Table 1) in each molecule.

Experimental

2-Methoxybenzohydrazide (0.1 mmol, 16.6 mg) and 3,5-diiodosalicylaldehyde (0.1 mmol, 37.4 mg) were stirred at 318 K in methanol (10 ml) for 30 min. The filtrate was kept in air for a few days depositing colorless block-like crystals of (I).

Refinement

The crystal studied was an inversion twin with a 0.59 (3):0.41 (3) domain ratio. The number of Friedel pairs in the data set is 3436. Atoms H2 and H4B were located in a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å, and with Uiso set to 0.08 Å2. All H atoms bound to carbon and oxygen were refined using riding models with d(C–H) = 0.93–0.96 Å, d(O–H) = 0.82 Å, Uiso = 1.2Ueq(C) and 1.5Ueq(O and methyl C).

Figures

Fig. 1.
The molecular structure of (I), showing the atom-numbering scheme and 30% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radii.

Crystal data

C15H12I2N2O3F(000) = 1968
Mr = 522.07Dx = 2.078 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 4242 reflections
a = 16.073 (2) Åθ = 2.3–24.5°
b = 15.628 (2) ŵ = 3.78 mm1
c = 13.284 (1) ÅT = 298 K
V = 3336.8 (6) Å3Block, colorless
Z = 80.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer7237 independent reflections
Radiation source: fine-focus sealed tube4902 reflections with I > 2σ(I)
graphiteRint = 0.053
ω scansθmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −20→20
Tmin = 0.432, Tmax = 0.469k = −19→19
26178 measured reflectionsl = −16→16

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101w = 1/[σ2(Fo2) + (0.0412P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
7237 reflectionsΔρmax = 0.78 e Å3
407 parametersΔρmin = −0.56 e Å3
3 restraintsAbsolute structure: Flack (1983), 3436 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.59 (3)

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
I30.40540 (3)0.37109 (4)0.59648 (6)0.0789 (2)
I40.75672 (4)0.29448 (4)0.71249 (6)0.0744 (2)
O40.4652 (3)0.5530 (4)0.6664 (5)0.0592 (16)
H40.47520.59740.69710.071*
O50.4563 (4)0.7984 (3)0.7103 (6)0.0738 (18)
O60.7003 (4)0.8732 (4)0.7109 (6)0.0745 (19)
N30.5663 (4)0.6711 (4)0.7246 (6)0.0492 (17)
N40.5871 (4)0.7542 (4)0.7391 (6)0.0552 (19)
C160.6078 (4)0.5270 (5)0.7135 (7)0.0428 (18)
C170.5299 (5)0.4972 (5)0.6787 (6)0.0430 (19)
C180.5183 (5)0.4121 (5)0.6577 (7)0.052 (2)
C190.5820 (5)0.3546 (5)0.6660 (6)0.048 (2)
H190.57400.29740.64930.057*
C200.6582 (5)0.3831 (5)0.6994 (6)0.047 (2)
C210.6718 (5)0.4676 (5)0.7198 (7)0.053 (2)
H210.72480.48560.73810.064*
C220.6248 (5)0.6155 (5)0.7341 (6)0.047 (2)
H220.67770.63250.75410.057*
C230.5297 (5)0.8171 (5)0.7244 (6)0.0452 (19)
C240.5589 (5)0.9062 (5)0.7306 (6)0.0455 (19)
C250.6422 (5)0.9340 (5)0.7234 (7)0.053 (2)
C260.6607 (7)1.0209 (6)0.7251 (8)0.074 (3)
H260.71541.03910.71710.089*
C270.6000 (9)1.0786 (6)0.7381 (7)0.085 (4)
H270.61371.13620.74310.102*
C280.5176 (8)1.0543 (7)0.7445 (7)0.083 (3)
H280.47581.09500.75180.100*
C290.4986 (6)0.9687 (6)0.7397 (6)0.061 (2)
H290.44300.95220.74280.073*
C300.7849 (5)0.8953 (7)0.6937 (8)0.080 (3)
H30A0.80550.92760.74990.119*
H30B0.78900.92920.63360.119*
H30C0.81730.84410.68600.119*
I10.81885 (3)0.63308 (4)0.55553 (6)0.0747 (2)
I20.46921 (4)0.71070 (4)0.43332 (6)0.0793 (2)
O10.7606 (3)0.4525 (4)0.4793 (5)0.0549 (16)
H10.74250.40410.48900.082*
O20.7669 (3)0.2033 (4)0.4301 (7)0.076 (2)
O30.5224 (3)0.1360 (3)0.4748 (5)0.0639 (16)
N10.6578 (4)0.3339 (4)0.4300 (5)0.0465 (16)
N20.6348 (4)0.2499 (4)0.4275 (6)0.0540 (17)
C10.6177 (4)0.4794 (5)0.4342 (6)0.0407 (18)
C20.6962 (5)0.5073 (5)0.4661 (6)0.046 (2)
C30.7075 (4)0.5914 (5)0.4888 (6)0.048 (2)
C40.6443 (5)0.6517 (5)0.4757 (6)0.052 (2)
H4A0.65370.70940.48830.063*
C50.5680 (5)0.6235 (5)0.4438 (7)0.053 (2)
C60.5548 (5)0.5392 (5)0.4207 (6)0.0451 (19)
H60.50350.52190.39580.054*
C70.6016 (5)0.3892 (5)0.4185 (7)0.048 (2)
H70.54860.37170.39960.057*
C80.6933 (5)0.1877 (5)0.4350 (7)0.0462 (19)
C90.6631 (5)0.0984 (5)0.4467 (6)0.044 (2)
C100.5797 (5)0.0735 (5)0.4667 (6)0.047 (2)
C110.5616 (6)−0.0131 (6)0.4790 (7)0.063 (2)
H110.5075−0.03000.49380.075*
C120.6220 (8)−0.0729 (6)0.4696 (8)0.077 (3)
H120.6084−0.13040.47660.093*
C130.7045 (7)−0.0501 (6)0.4495 (7)0.074 (3)
H130.7460−0.09130.44370.089*
C140.7219 (6)0.0346 (5)0.4387 (6)0.052 (2)
H140.77660.05030.42520.062*
C150.4365 (5)0.1115 (6)0.4888 (7)0.066 (3)
H15A0.42930.08800.55500.099*
H15B0.42150.06940.43940.099*
H15C0.40150.16090.48130.099*
H20.5807 (15)0.237 (5)0.435 (7)0.080*
H4B0.639 (2)0.770 (5)0.754 (7)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I30.0459 (3)0.0612 (4)0.1295 (6)−0.0160 (3)−0.0114 (4)−0.0033 (4)
I40.0618 (4)0.0584 (4)0.1029 (5)0.0198 (3)−0.0071 (4)−0.0048 (4)
O40.034 (3)0.054 (3)0.089 (5)−0.002 (3)0.003 (3)−0.001 (3)
O50.056 (4)0.053 (4)0.112 (5)0.002 (3)0.003 (4)0.002 (4)
O60.048 (4)0.067 (4)0.108 (6)−0.011 (3)0.003 (4)0.010 (4)
N30.041 (4)0.044 (4)0.063 (5)−0.004 (3)0.002 (4)−0.006 (4)
N40.045 (4)0.038 (4)0.083 (6)−0.001 (3)−0.012 (4)−0.012 (4)
C160.029 (4)0.043 (4)0.056 (5)0.008 (3)−0.007 (4)0.006 (4)
C170.045 (5)0.042 (4)0.042 (5)−0.003 (4)0.009 (4)−0.003 (4)
C180.038 (4)0.056 (5)0.060 (6)−0.006 (4)0.001 (4)0.016 (5)
C190.057 (5)0.040 (4)0.047 (5)−0.009 (4)0.009 (4)0.008 (4)
C200.046 (4)0.045 (5)0.051 (5)0.009 (4)0.003 (4)−0.002 (4)
C210.039 (4)0.056 (5)0.064 (6)−0.009 (4)0.013 (4)−0.005 (5)
C220.046 (5)0.043 (5)0.053 (6)−0.009 (4)−0.005 (4)−0.009 (4)
C230.042 (5)0.053 (5)0.041 (5)−0.006 (4)0.004 (4)−0.003 (4)
C240.047 (4)0.050 (5)0.039 (5)−0.001 (4)0.007 (4)0.006 (4)
C250.056 (5)0.054 (5)0.048 (5)−0.002 (4)−0.005 (4)0.006 (4)
C260.093 (7)0.053 (6)0.076 (7)−0.026 (6)−0.015 (6)0.008 (6)
C270.152 (12)0.038 (5)0.065 (7)−0.015 (7)0.019 (7)0.002 (5)
C280.111 (9)0.064 (7)0.075 (8)0.026 (6)0.023 (7)0.003 (5)
C290.079 (6)0.056 (6)0.047 (6)−0.003 (5)0.005 (5)0.003 (4)
C300.055 (6)0.115 (8)0.069 (7)−0.009 (6)0.000 (5)0.016 (6)
I10.0441 (3)0.0585 (4)0.1215 (6)−0.0146 (3)−0.0043 (3)−0.0101 (4)
I20.0761 (4)0.0635 (4)0.0985 (5)0.0285 (3)−0.0265 (4)−0.0121 (4)
O10.031 (3)0.045 (3)0.088 (5)0.004 (2)−0.002 (3)0.000 (3)
O20.033 (3)0.058 (4)0.137 (6)0.003 (3)0.002 (4)−0.004 (4)
O30.045 (3)0.051 (3)0.096 (5)−0.003 (3)0.005 (3)0.000 (3)
N10.039 (4)0.042 (4)0.058 (4)0.001 (3)−0.001 (3)−0.007 (4)
N20.041 (4)0.039 (4)0.082 (5)−0.007 (3)−0.004 (4)−0.003 (4)
C10.039 (4)0.037 (4)0.047 (5)−0.002 (3)0.003 (4)−0.007 (4)
C20.035 (4)0.050 (5)0.052 (5)0.002 (4)0.007 (4)0.005 (4)
C30.038 (4)0.051 (5)0.053 (5)−0.006 (4)0.001 (4)−0.005 (4)
C40.059 (6)0.033 (4)0.065 (6)0.001 (4)−0.004 (5)−0.009 (4)
C50.055 (5)0.048 (5)0.057 (6)0.003 (4)−0.004 (4)0.008 (5)
C60.040 (4)0.061 (5)0.035 (5)0.008 (4)−0.013 (4)−0.004 (4)
C70.035 (4)0.056 (5)0.053 (5)−0.012 (4)−0.005 (4)0.007 (4)
C80.043 (5)0.037 (4)0.058 (5)0.002 (4)0.007 (4)−0.008 (4)
C90.052 (5)0.045 (4)0.034 (5)0.008 (4)0.005 (4)0.000 (4)
C100.062 (5)0.043 (5)0.035 (5)−0.013 (4)−0.007 (4)0.003 (4)
C110.070 (6)0.053 (6)0.064 (6)−0.014 (5)−0.014 (5)0.001 (5)
C120.127 (10)0.038 (5)0.068 (7)−0.007 (6)−0.009 (6)−0.002 (5)
C130.112 (9)0.043 (5)0.068 (7)0.002 (6)−0.018 (6)0.001 (5)
C140.061 (5)0.043 (5)0.051 (5)0.004 (4)−0.001 (5)−0.008 (4)
C150.054 (5)0.080 (6)0.065 (6)−0.029 (5)−0.002 (5)−0.002 (5)

Geometric parameters (Å, °)

I3—C182.090 (8)I1—C32.101 (7)
I4—C202.111 (7)I2—C52.098 (8)
O4—C171.367 (9)O1—C21.355 (8)
O4—H40.8200O1—H10.8200
O5—C231.229 (9)O2—C81.210 (9)
O6—C251.342 (10)O3—C101.348 (10)
O6—C301.421 (10)O3—C151.445 (9)
N3—C221.287 (10)N1—C71.259 (10)
N3—N41.354 (8)N1—N21.364 (8)
N4—C231.362 (10)N2—C81.356 (9)
N4—H4B0.89 (5)N2—H20.90 (3)
C16—C211.389 (10)C1—C61.389 (10)
C16—C171.414 (10)C1—C21.400 (10)
C16—C221.437 (10)C1—C71.448 (10)
C17—C181.371 (11)C2—C31.360 (10)
C18—C191.366 (11)C3—C41.396 (11)
C19—C201.377 (11)C4—C51.370 (11)
C19—H190.9300C4—H4A0.9300
C20—C211.365 (10)C5—C61.369 (10)
C21—H210.9300C6—H60.9300
C22—H220.9300C7—H70.9300
C23—C241.472 (11)C8—C91.485 (11)
C24—C291.382 (12)C9—C141.379 (10)
C24—C251.412 (11)C9—C101.421 (11)
C25—C261.390 (12)C10—C111.393 (11)
C26—C271.339 (15)C11—C121.353 (13)
C26—H260.9300C11—H110.9300
C27—C281.381 (15)C12—C131.399 (14)
C27—H270.9300C12—H120.9300
C28—C291.374 (12)C13—C141.360 (12)
C28—H280.9300C13—H130.9300
C29—H290.9300C14—H140.9300
C30—H30A0.9600C15—H15A0.9600
C30—H30B0.9600C15—H15B0.9600
C30—H30C0.9600C15—H15C0.9600
C17—O4—H4109.4C2—O1—H1109.5
C25—O6—C30120.9 (7)C10—O3—C15118.1 (6)
C22—N3—N4116.9 (7)C7—N1—N2117.7 (7)
N3—N4—C23120.3 (7)C8—N2—N1120.1 (6)
N3—N4—H4B121 (6)C8—N2—H2120 (6)
C23—N4—H4B118 (6)N1—N2—H2118 (6)
C21—C16—C17117.1 (7)C6—C1—C2119.0 (7)
C21—C16—C22119.4 (7)C6—C1—C7120.5 (7)
C17—C16—C22123.3 (7)C2—C1—C7120.5 (7)
O4—C17—C18119.5 (7)O1—C2—C3118.7 (7)
O4—C17—C16120.1 (7)O1—C2—C1122.0 (7)
C18—C17—C16120.4 (7)C3—C2—C1119.2 (7)
C19—C18—C17121.3 (8)C2—C3—C4121.8 (7)
C19—C18—I3118.7 (7)C2—C3—I1120.4 (6)
C17—C18—I3119.6 (6)C4—C3—I1117.6 (6)
C18—C19—C20118.7 (8)C5—C4—C3118.2 (8)
C18—C19—H19120.7C5—C4—H4A120.9
C20—C19—H19120.7C3—C4—H4A120.9
C21—C20—C19121.3 (8)C6—C5—C4121.2 (8)
C21—C20—I4119.9 (6)C6—C5—I2119.5 (6)
C19—C20—I4118.8 (6)C4—C5—I2119.3 (6)
C20—C21—C16121.0 (8)C5—C6—C1120.4 (7)
C20—C21—H21119.5C5—C6—H6119.8
C16—C21—H21119.5C1—C6—H6119.8
N3—C22—C16119.5 (7)N1—C7—C1121.5 (8)
N3—C22—H22120.3N1—C7—H7119.2
C16—C22—H22120.3C1—C7—H7119.2
O5—C23—N4120.1 (7)O2—C8—N2121.9 (7)
O5—C23—C24122.6 (7)O2—C8—C9121.0 (7)
N4—C23—C24117.3 (7)N2—C8—C9117.1 (7)
C29—C24—C25117.0 (8)C14—C9—C10117.6 (8)
C29—C24—C23116.7 (7)C14—C9—C8116.6 (7)
C25—C24—C23126.2 (7)C10—C9—C8125.9 (7)
O6—C25—C26123.0 (8)O3—C10—C11123.5 (8)
O6—C25—C24116.7 (7)O3—C10—C9117.4 (7)
C26—C25—C24120.2 (9)C11—C10—C9119.0 (8)
C27—C26—C25120.3 (10)C12—C11—C10120.7 (9)
C27—C26—H26119.9C12—C11—H11119.7
C25—C26—H26119.9C10—C11—H11119.7
C26—C27—C28121.5 (9)C11—C12—C13121.5 (9)
C26—C27—H27119.3C11—C12—H12119.3
C28—C27—H27119.3C13—C12—H12119.3
C29—C28—C27118.6 (10)C14—C13—C12117.5 (10)
C29—C28—H28120.7C14—C13—H13121.2
C27—C28—H28120.7C12—C13—H13121.2
C28—C29—C24122.4 (9)C13—C14—C9123.7 (9)
C28—C29—H29118.8C13—C14—H14118.1
C24—C29—H29118.8C9—C14—H14118.1
O6—C30—H30A109.5O3—C15—H15A109.5
O6—C30—H30B109.5O3—C15—H15B109.5
H30A—C30—H30B109.5H15A—C15—H15B109.5
O6—C30—H30C109.5O3—C15—H15C109.5
H30A—C30—H30C109.5H15A—C15—H15C109.5
H30B—C30—H30C109.5H15B—C15—H15C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4···N30.821.902.577 (8)139
O1—H1···N10.821.922.568 (8)136
N2—H2···O30.90 (3)1.91 (6)2.613 (8)134 (8)
N4—H4B···O60.89 (5)1.98 (7)2.629 (9)128 (7)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2624).

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