(E)-N′-(2-Hy­droxy-3,5-diiodo­benzyl­idene)-3-methyl­benzohydrazide

Tang, C.-B.

doi:10.1107/S160053681200387X

organic compounds

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Volume 68| Part 3| March 2012| Page o603

doi:10.1107/S160053681200387X

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(E)-N′-(2-Hydroxy-3,5-diiodobenzylidene)-3-methylbenzohydrazide

Chun-Bao Tang ^a ^*

^aDepartment of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China
^*Correspondence e-mail: chunbao_tang@yahoo.cn

(Received 28 January 2012; accepted 29 January 2012; online 4 February 2012)

In the title compound, C₁₅H₁₂I₂N₂O₂, the dihedral angle between the benzene rings is 26.5 (3)° and the molecule has an E configuration about the C=N bond. An intramolecular O—H⋯N hydrogen bond is observed in the molecule. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming chains along the c axis.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ); Pyta et al. (2010 ); Angelusiu et al. (2010 ). For related structures, see: Fun et al. (2008 ); Singh & Singh (2010 ); Ahmad et al. (2010 ); Tang (2010 , 2011 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₂I₂N₂O₂
M_r = 506.07
Monoclinic, P 2₁ /c
a = 14.778 (3) Å
b = 11.764 (3) Å
c = 9.8480 (19) Å
β = 102.191 (2)°
V = 1673.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 3.76 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.567, T_max = 0.602
11923 measured reflections
3430 independent reflections
2072 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.175
S = 1.02
3430 reflections
196 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 2.01 e Å⁻³
Δρ_min = −1.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.572 (8)	146
N2—H2⋯O2ⁱ	0.90 (1)	1.93 (2)	2.800 (9)	162 (6)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681200387X/su2373sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200387X/su2373Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681200387X/su2373Isup3.cml

checkCIF report

Comment top

Hydrazone compounds have received much attention in biological and structural chemistry in the last few years (Rasras et al., 2010; Pyta et al., 2010; Angelusiu et al., 2010; Fun et al., 2008; Singh & Singh, 2010; Ahmad et al., 2010). As a continuation of our work on the structural study on such compounds (Tang, 2010, 2011), the author reports herein the crystal structure of the new title hydrazone compound.

In the title compound (Fig. 1), the dihedral angle between the two benzene rings is 26.5 (3)°. An intramolecular O1—H1···N1 hydrogen bond (Table 1) is observed in the molecule, which has an E configuration about the N1═C7 bond. Bond lengths in the compound are normal (Allen et al., 1987) and comparable to those in the similar compounds mentioned above. In the crystal, molecules are linked through intermolecular N—H···O hydrogen bonds, forming chains along the c axis (Fig. 2 and Table 1).

Related literature top

For general background to hydrazones, see: Rasras et al. (2010); Pyta et al. (2010); Angelusiu et al. (2010). For related structures, see: Fun et al. (2008); Singh & Singh (2010); Ahmad et al. (2010); Tang (2010, 2011). For reference bond-length data, see: Allen et al. (1987).

Experimental top

2-Hydroxy-3,5-diiodobenzaldehyde (0.1 mmol, 37.5 mg) and 3-methylbenzohydrazide (0.1 mmol, 15.0 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 10 min to give a clear colourless solution. Colourless needle-shaped crystals of the compound were formed by slow evaporation of the solvent over several days.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering and displacement ellipsoids drawn at the 30% probability level. The intramolecular O—H···N hydrogen bond is shown as a dashed line (see Table 1 for details).
	Fig. 2. Crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

(E)-N'-(2-Hydroxy-3,5-diiodobenzylidene)-3-methylbenzohydrazide top

Crystal data top

C₁₅H₁₂I₂N₂O₂	F(000) = 952
M_r = 506.07	D_x = 2.009 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2661 reflections
a = 14.778 (3) Å	θ = 2.2–24.4°
b = 11.764 (3) Å	µ = 3.76 mm⁻¹
c = 9.8480 (19) Å	T = 298 K
β = 102.191 (2)°	Cut from needle, colourless
V = 1673.4 (6) Å³	0.17 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3430 independent reflections
Radiation source: fine-focus sealed tube	2072 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ω scans	θ_max = 26.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→18
T_min = 0.567, T_max = 0.602	k = −14→14
11923 measured reflections	l = −12→12

Refinement top

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.058P)² + 13.9544P] where P = (F_o² + 2F_c²)/3
3430 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 2.01 e Å⁻³
1 restraint	Δρ_min = −1.21 e Å⁻³

Crystal data top

C₁₅H₁₂I₂N₂O₂	V = 1673.4 (6) Å³
M_r = 506.07	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.778 (3) Å	µ = 3.76 mm⁻¹
b = 11.764 (3) Å	T = 298 K
c = 9.8480 (19) Å	0.17 × 0.15 × 0.15 mm
β = 102.191 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3430 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2072 reflections with I > 2σ(I)
T_min = 0.567, T_max = 0.602	R_int = 0.045
11923 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	1 restraint
wR(F²) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.058P)² + 13.9544P] where P = (F_o² + 2F_c²)/3
3430 reflections	Δρ_max = 2.01 e Å⁻³
196 parameters	Δρ_min = −1.21 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
I1	0.35741 (6)	0.46000 (8)	0.09441 (9)	0.0923 (4)
I2	0.26264 (6)	0.40585 (9)	0.65569 (12)	0.0979 (4)
N1	0.6613 (5)	0.2920 (6)	0.4785 (7)	0.0399 (17)
N2	0.7486 (5)	0.2539 (6)	0.5352 (7)	0.0410 (17)
O1	0.5439 (5)	0.3715 (6)	0.2693 (6)	0.0589 (18)
H1	0.5930	0.3439	0.3106	0.088*
O2	0.7851 (4)	0.2492 (7)	0.3260 (6)	0.0599 (19)
C1	0.5105 (6)	0.3476 (7)	0.4956 (10)	0.044 (2)
C2	0.4846 (6)	0.3768 (7)	0.3551 (9)	0.045 (2)
C3	0.3942 (7)	0.4123 (9)	0.3033 (11)	0.059 (3)
C4	0.3331 (7)	0.4219 (8)	0.3891 (13)	0.066 (3)
H4	0.2733	0.4478	0.3532	0.080*
C5	0.3581 (6)	0.3939 (9)	0.5277 (13)	0.061 (3)
C6	0.4465 (6)	0.3558 (8)	0.5815 (11)	0.055 (2)
H6	0.4636	0.3355	0.6747	0.066*
C7	0.6045 (6)	0.3093 (7)	0.5559 (9)	0.043 (2)
H7	0.6225	0.2976	0.6512	0.052*
C8	0.8065 (6)	0.2322 (7)	0.4513 (8)	0.039 (2)
C9	0.8987 (6)	0.1848 (7)	0.5190 (8)	0.0377 (19)
C10	0.9737 (7)	0.2119 (9)	0.4621 (11)	0.059 (3)
H10	0.9661	0.2599	0.3855	0.070*
C11	1.0589 (8)	0.1685 (11)	0.5179 (14)	0.075 (3)
H11	1.1091	0.1863	0.4787	0.090*
C12	1.0708 (7)	0.0988 (11)	0.6311 (12)	0.072 (3)
H12	1.1297	0.0711	0.6691	0.086*
C13	0.9977 (8)	0.0684 (10)	0.6908 (10)	0.067 (3)
C14	0.9116 (7)	0.1147 (8)	0.6307 (9)	0.049 (2)
H14	0.8610	0.0968	0.6689	0.059*
C15	1.0119 (11)	−0.0117 (13)	0.8132 (13)	0.108 (5)
H15A	1.0718	0.0011	0.8714	0.162*
H15B	1.0078	−0.0888	0.7805	0.162*
H15C	0.9650	0.0015	0.8656	0.162*
H2	0.767 (4)	0.239 (6)	0.626 (2)	0.018 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0839 (6)	0.0968 (7)	0.0776 (6)	0.0291 (5)	−0.0248 (4)	0.0073 (5)
I2	0.0542 (5)	0.1061 (8)	0.1439 (9)	−0.0029 (5)	0.0449 (5)	−0.0132 (6)
N1	0.037 (4)	0.044 (4)	0.036 (4)	0.009 (3)	0.001 (3)	0.002 (3)
N2	0.041 (4)	0.056 (5)	0.024 (3)	0.010 (3)	0.002 (3)	0.001 (3)
O1	0.054 (4)	0.072 (5)	0.044 (4)	0.016 (4)	−0.005 (3)	0.002 (3)
O2	0.058 (4)	0.101 (5)	0.023 (3)	0.011 (4)	0.014 (3)	0.005 (3)
C1	0.039 (5)	0.033 (4)	0.058 (6)	−0.001 (4)	0.003 (4)	−0.008 (4)
C2	0.044 (5)	0.040 (5)	0.046 (5)	0.006 (4)	−0.002 (4)	−0.013 (4)
C3	0.061 (6)	0.053 (6)	0.056 (6)	0.008 (5)	−0.007 (5)	−0.012 (5)
C4	0.043 (6)	0.045 (6)	0.101 (9)	0.005 (5)	−0.008 (6)	−0.015 (6)
C5	0.035 (5)	0.053 (6)	0.093 (8)	−0.007 (5)	0.008 (5)	−0.013 (6)
C6	0.044 (5)	0.049 (6)	0.071 (7)	0.000 (5)	0.012 (5)	−0.007 (5)
C7	0.044 (5)	0.044 (5)	0.041 (5)	0.006 (4)	0.007 (4)	−0.004 (4)
C8	0.045 (5)	0.049 (5)	0.020 (4)	−0.001 (4)	0.006 (3)	−0.002 (3)
C9	0.040 (5)	0.045 (5)	0.027 (4)	0.003 (4)	0.006 (3)	−0.006 (4)
C10	0.052 (6)	0.058 (6)	0.064 (6)	0.002 (5)	0.007 (5)	0.000 (5)
C11	0.049 (7)	0.090 (9)	0.091 (9)	−0.008 (6)	0.028 (6)	−0.011 (7)
C12	0.039 (6)	0.101 (9)	0.070 (8)	0.017 (6)	0.000 (5)	−0.025 (7)
C13	0.074 (8)	0.078 (8)	0.042 (5)	0.027 (6)	−0.008 (5)	−0.002 (5)
C14	0.051 (5)	0.065 (6)	0.032 (5)	0.015 (5)	0.009 (4)	−0.008 (4)
C15	0.114 (11)	0.133 (13)	0.069 (8)	0.070 (10)	0.001 (8)	0.016 (8)

Geometric parameters (Å, º) top

I1—C3	2.090 (10)	C6—H6	0.9300
I2—C5	2.085 (11)	C7—H7	0.9300
N1—C7	1.264 (10)	C8—C9	1.493 (11)
N1—N2	1.368 (9)	C9—C14	1.356 (12)
N2—C8	1.334 (10)	C9—C10	1.381 (13)
N2—H2	0.897 (10)	C10—C11	1.362 (15)
O1—C2	1.341 (11)	C10—H10	0.9300
O1—H1	0.8200	C11—C12	1.365 (17)
O2—C8	1.224 (9)	C11—H11	0.9300
C1—C2	1.399 (12)	C12—C13	1.381 (16)
C1—C6	1.399 (13)	C12—H12	0.9300
C1—C7	1.461 (12)	C13—C14	1.395 (13)
C2—C3	1.390 (13)	C13—C15	1.510 (16)
C3—C4	1.365 (15)	C14—H14	0.9300
C4—C5	1.377 (16)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.377 (13)	C15—H15C	0.9600

C7—N1—N2	119.7 (7)	O2—C8—C9	121.9 (8)
C8—N2—N1	118.8 (6)	N2—C8—C9	116.1 (6)
C8—N2—H2	119 (4)	C14—C9—C10	118.9 (8)
N1—N2—H2	123 (4)	C14—C9—C8	123.2 (8)
C2—O1—H1	109.5	C10—C9—C8	117.9 (8)
C2—C1—C6	120.2 (8)	C11—C10—C9	120.1 (10)
C2—C1—C7	121.0 (8)	C11—C10—H10	119.9
C6—C1—C7	118.8 (8)	C9—C10—H10	119.9
O1—C2—C3	119.2 (8)	C10—C11—C12	120.3 (11)
O1—C2—C1	122.2 (8)	C10—C11—H11	119.9
C3—C2—C1	118.5 (9)	C12—C11—H11	119.9
C4—C3—C2	120.5 (10)	C11—C12—C13	121.7 (10)
C4—C3—I1	121.2 (8)	C11—C12—H12	119.2
C2—C3—I1	118.1 (8)	C13—C12—H12	119.2
C3—C4—C5	121.3 (10)	C12—C13—C14	116.4 (10)
C3—C4—H4	119.3	C12—C13—C15	120.8 (11)
C5—C4—H4	119.3	C14—C13—C15	122.8 (11)
C6—C5—C4	119.6 (10)	C9—C14—C13	122.7 (10)
C6—C5—I2	119.8 (9)	C9—C14—H14	118.6
C4—C5—I2	120.6 (8)	C13—C14—H14	118.6
C5—C6—C1	119.8 (10)	C13—C15—H15A	109.5
C5—C6—H6	120.1	C13—C15—H15B	109.5
C1—C6—H6	120.1	H15A—C15—H15B	109.5
N1—C7—C1	120.0 (8)	C13—C15—H15C	109.5
N1—C7—H7	120.0	H15A—C15—H15C	109.5
C1—C7—H7	120.0	H15B—C15—H15C	109.5
O2—C8—N2	122.1 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.572 (8)	146
N2—H2···O2ⁱ	0.90 (1)	1.93 (2)	2.800 (9)	162 (6)

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂I₂N₂O₂
M_r	506.07
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	14.778 (3), 11.764 (3), 9.8480 (19)
β (°)	102.191 (2)
V (Å³)	1673.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.76
Crystal size (mm)	0.17 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.567, 0.602
No. of measured, independent and observed [I > 2σ(I)] reflections	11923, 3430, 2072
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.175, 1.02
No. of reflections	3430
No. of parameters	196
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.058P)² + 13.9544P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	2.01, −1.21

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.572 (8)	146
N2—H2···O2ⁱ	0.897 (10)	1.93 (2)	2.800 (9)	162 (6)

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

Financial support from the Jiaying University research fund is gratefully acknowledged.

References

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