(E)-N′-(2-Hy­droxy-3,5-diiodo­benzyl­idene)nicotinohydrazide acetonitrile monosolvate

Sun, S.-S.; Liu, S.-Y.; Zheng, T.-T.; Wang, X.-L.

doi:10.1107/S1600536811020770

organic compounds

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Volume 67| Part 7| July 2011| Page o1624

doi:10.1107/S1600536811020770

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(E)-N′-(2-Hydroxy-3,5-diiodobenzylidene)nicotinohydrazide acetonitrile monosolvate

Shan-Shan Sun,^a Shi-Yong Liu,^a ^* Ting-Ting Zheng ^a and Xiao-Ling Wang ^b

^aCollege of Chemistry and Pharmacy, Taizhou University, Taizhou Zhejiang 317000, People's Republic of China, and ^bDepartment of Chemistry, Liaoning Normal University, Dalian 116029, People's Republic of China
^*Correspondence e-mail: liushiyong2010@yahoo.cn

(Received 25 May 2011; accepted 30 May 2011; online 11 June 2011)

In the hydrazone molecule of the title compound, C₁₃H₉I₂N₃O₂·CH₃CN, the aromatic rings form a dihedral angle of 9.4 (3)°. In the crystal structure, intermolecular I⋯N interactions [3.099 (4) Å] link hydrogen-bonded aggregates of the hydrozone and solvent molecules related by translation along the b axis into chains. An intramolecular O—H⋯N hydrogen bond forms an S(6) ring.

Related literature

For the crystal structures of hydrazones recently reported by us, see: Liu & You (2010a ,b ,c ); Liu & Wang (2010a ,b ; 2011 ).

Experimental

Crystal data

C₁₃H₉I₂N₃O₂·C₂H₃N
M_r = 534.09
Monoclinic, P 2₁ /n
a = 11.1347 (13) Å
b = 13.3721 (16) Å
c = 11.9999 (15) Å
β = 104.083 (6)°
V = 1733.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 3.64 mm⁻¹
T = 298 K
0.23 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.488, T_max = 0.529
10053 measured reflections
3546 independent reflections
2730 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.062
S = 1.01
3546 reflections
213 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.37 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	1.86	2.584 (4)	147
N2—H2⋯N4	0.90 (1)	2.22 (2)	3.076 (5)	160 (4)

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020770/cv5102sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020770/cv5102Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020770/cv5102Isup3.cml

checkCIF report

Comment top

In continuation of our structural studies of hydrazone derivatives (Liu & You, 2010a,b,c; Liu & Wang, 2010a,b; 2011), we present here the title compound (I).

In the asymmetric part of (I) (Fig. 1), the acetonitrile molecule is linked to the hydrazone molecule through intermolecular N–H···N hydrogen bond (Table 1). An intramolecular O—H···N hydrogen bond (Table 1) affects the molecular conformation - the dihedral angle between the C1–C6 benzene ring and the C9–C13/N3 pyridine ring is 9.4 (3)°.

In the crystal structure, there is I1···N3(x, -1 + y, z) [3.099 (4) Å] interaction, which link the molecules into chains along b axis.

Related literature top

For the crystal structures of hydrazones recently reported by us, see: Liu & You (2010a,b,c); Liu & Wang (2010a,b; 2011).

Experimental top

The title compound was prepared by the condensation reaction of 2-hydroxy-3,5-diiodobenzaldehyde (1.0 mmol, 0.374 g) and nicotinohydrazide (1.0 mmol, 0.137 g) in acetonitrile (50 ml) at ambient temperature. Colourless block-shaped single crystals suitable for X-ray structural determination were obtained by slow evaporation of the solution for a few days.

Computing details top

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

Figures top

Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as spheres of arbitrary radius and the hydrogen bonds are drawn as dashed lines.

(E)-N'-(2-Hydroxy-3,5-diiodobenzylidene)nicotinohydrazide acetonitrile monosolvate top

Crystal data top

C₁₃H₉I₂N₃O₂·C₂H₃N	F(000) = 1008
M_r = 534.09	D_x = 2.047 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.1347 (13) Å	Cell parameters from 2928 reflections
b = 13.3721 (16) Å	θ = 2.4–26.0°
c = 11.9999 (15) Å	µ = 3.64 mm⁻¹
β = 104.083 (6)°	T = 298 K
V = 1733.0 (4) Å³	Block, colourless
Z = 4	0.23 × 0.22 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3546 independent reflections
Radiation source: fine-focus sealed tube	2730 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 26.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→13
T_min = 0.488, T_max = 0.529	k = −15→16
10053 measured reflections	l = −9→14

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0273P)²] where P = (F_o² + 2F_c²)/3
3546 reflections	(Δ/σ)_max < 0.001
213 parameters	Δρ_max = 0.41 e Å⁻³
1 restraint	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₃H₉I₂N₃O₂·C₂H₃N	V = 1733.0 (4) Å³
M_r = 534.09	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.1347 (13) Å	µ = 3.64 mm⁻¹
b = 13.3721 (16) Å	T = 298 K
c = 11.9999 (15) Å	0.23 × 0.22 × 0.20 mm
β = 104.083 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3546 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2730 reflections with I > 2σ(I)
T_min = 0.488, T_max = 0.529	R_int = 0.031
10053 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	1 restraint
wR(F²) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.41 e Å⁻³
3546 reflections	Δρ_min = −0.37 e Å⁻³
213 parameters

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	0.58225 (2)	0.137781 (18)	0.14099 (2)	0.04871 (9)
I2	0.97606 (3)	0.30924 (2)	−0.06800 (2)	0.05637 (10)
N1	0.5759 (3)	0.5602 (2)	0.1531 (3)	0.0441 (8)
N2	0.5445 (3)	0.6581 (2)	0.1681 (3)	0.0461 (8)
N3	0.4412 (4)	0.9562 (2)	0.2073 (3)	0.0625 (10)
N4	0.7239 (4)	0.8004 (3)	0.0881 (4)	0.0773 (12)
O1	0.5386 (3)	0.37009 (19)	0.1633 (3)	0.0524 (7)
H1	0.5268	0.4298	0.1716	0.079*
O2	0.4105 (3)	0.6067 (2)	0.2699 (3)	0.0652 (8)
C1	0.6974 (3)	0.4418 (2)	0.0834 (3)	0.0375 (8)
C2	0.6354 (3)	0.3585 (3)	0.1150 (3)	0.0394 (8)
C3	0.6742 (3)	0.2631 (3)	0.0952 (3)	0.0399 (9)
C4	0.7714 (3)	0.2493 (3)	0.0444 (3)	0.0413 (9)
H4	0.7969	0.1850	0.0318	0.050*
C5	0.8309 (3)	0.3311 (3)	0.0123 (3)	0.0399 (9)
C6	0.7952 (3)	0.4261 (3)	0.0316 (3)	0.0418 (9)
H6	0.8364	0.4805	0.0101	0.050*
C7	0.6612 (3)	0.5441 (3)	0.1014 (3)	0.0440 (9)
H7	0.7004	0.5975	0.0752	0.053*
C8	0.4560 (3)	0.6742 (3)	0.2269 (3)	0.0428 (9)
C9	0.4165 (3)	0.7803 (3)	0.2325 (3)	0.0392 (8)
C10	0.3099 (4)	0.7986 (3)	0.2676 (4)	0.0538 (10)
H10	0.2664	0.7459	0.2898	0.065*
C11	0.2676 (4)	0.8956 (3)	0.2697 (4)	0.0628 (12)
H11	0.1944	0.9095	0.2910	0.075*
C12	0.3370 (4)	0.9702 (3)	0.2396 (4)	0.0613 (12)
H12	0.3092	1.0355	0.2419	0.074*
C13	0.4789 (4)	0.8619 (3)	0.2048 (3)	0.0518 (10)
H13	0.5522	0.8504	0.1828	0.062*
C14	0.8500 (5)	0.9474 (3)	0.0420 (4)	0.0834 (16)
H14A	0.8874	0.9288	−0.0191	0.125*
H14B	0.9135	0.9650	0.1088	0.125*
H14C	0.7963	1.0037	0.0184	0.125*
C15	0.7793 (4)	0.8646 (3)	0.0688 (4)	0.0595 (11)
H2	0.580 (4)	0.707 (2)	0.135 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.05615 (17)	0.03602 (14)	0.06087 (19)	−0.00160 (11)	0.02760 (13)	0.00167 (12)
I2	0.05261 (17)	0.05701 (18)	0.0699 (2)	0.00518 (13)	0.03507 (14)	0.00061 (14)
N1	0.0471 (19)	0.0306 (16)	0.057 (2)	0.0023 (13)	0.0177 (16)	−0.0047 (14)
N2	0.052 (2)	0.0276 (17)	0.064 (2)	0.0024 (14)	0.0242 (17)	−0.0030 (15)
N3	0.075 (3)	0.0336 (18)	0.085 (3)	0.0053 (17)	0.032 (2)	−0.0059 (18)
N4	0.059 (3)	0.066 (3)	0.115 (4)	0.001 (2)	0.038 (2)	0.005 (3)
O1	0.0511 (17)	0.0445 (15)	0.0723 (19)	0.0018 (13)	0.0359 (14)	−0.0019 (15)
O2	0.072 (2)	0.0430 (16)	0.094 (2)	−0.0027 (15)	0.0471 (18)	0.0030 (16)
C1	0.044 (2)	0.0317 (19)	0.039 (2)	−0.0001 (15)	0.0135 (16)	−0.0021 (15)
C2	0.040 (2)	0.041 (2)	0.040 (2)	0.0008 (16)	0.0158 (17)	−0.0008 (17)
C3	0.048 (2)	0.0331 (19)	0.042 (2)	0.0001 (16)	0.0179 (17)	0.0019 (16)
C4	0.049 (2)	0.0339 (19)	0.046 (2)	0.0074 (17)	0.0198 (18)	−0.0004 (17)
C5	0.038 (2)	0.043 (2)	0.042 (2)	0.0032 (16)	0.0184 (17)	−0.0005 (17)
C6	0.046 (2)	0.0345 (19)	0.048 (2)	−0.0018 (16)	0.0172 (18)	0.0011 (17)
C7	0.050 (2)	0.0325 (19)	0.053 (2)	0.0013 (16)	0.0198 (19)	0.0016 (17)
C8	0.047 (2)	0.035 (2)	0.049 (2)	−0.0027 (17)	0.0179 (19)	−0.0044 (17)
C9	0.042 (2)	0.0356 (19)	0.044 (2)	−0.0013 (15)	0.0177 (17)	−0.0080 (17)
C10	0.050 (2)	0.047 (2)	0.069 (3)	−0.0041 (19)	0.023 (2)	−0.011 (2)
C11	0.043 (2)	0.061 (3)	0.088 (3)	0.005 (2)	0.024 (2)	−0.019 (3)
C12	0.064 (3)	0.044 (2)	0.076 (3)	0.008 (2)	0.017 (2)	−0.015 (2)
C13	0.056 (3)	0.037 (2)	0.070 (3)	−0.0006 (18)	0.031 (2)	−0.005 (2)
C14	0.114 (4)	0.052 (3)	0.098 (4)	0.001 (3)	0.052 (3)	0.009 (3)
C15	0.060 (3)	0.054 (3)	0.072 (3)	0.012 (2)	0.030 (2)	0.003 (2)

Geometric parameters (Å, º) top

I1—C3	2.106 (3)	C4—H4	0.9300
I2—C5	2.094 (3)	C5—C6	1.367 (5)
N1—C7	1.273 (4)	C6—H6	0.9300
N1—N2	1.377 (4)	C7—H7	0.9300
N2—C8	1.362 (5)	C8—C9	1.492 (5)
N2—H2	0.897 (10)	C9—C10	1.375 (5)
N3—C12	1.323 (5)	C9—C13	1.377 (5)
N3—C13	1.332 (5)	C10—C11	1.382 (5)
N4—C15	1.114 (5)	C10—H10	0.9300
O1—C2	1.351 (4)	C11—C12	1.364 (6)
O1—H1	0.8200	C11—H11	0.9300
O2—C8	1.210 (4)	C12—H12	0.9300
C1—C6	1.395 (5)	C13—H13	0.9300
C1—C2	1.411 (5)	C14—C15	1.440 (6)
C1—C7	1.457 (5)	C14—H14A	0.9600
C2—C3	1.385 (5)	C14—H14B	0.9600
C3—C4	1.377 (5)	C14—H14C	0.9600
C4—C5	1.382 (5)

C7—N1—N2	117.9 (3)	C1—C7—H7	120.1
C8—N2—N1	117.2 (3)	O2—C8—N2	122.3 (3)
C8—N2—H2	124 (3)	O2—C8—C9	122.1 (3)
N1—N2—H2	118 (3)	N2—C8—C9	115.6 (3)
C12—N3—C13	116.4 (4)	C10—C9—C13	117.2 (3)
C2—O1—H1	109.5	C10—C9—C8	118.0 (3)
C6—C1—C2	119.1 (3)	C13—C9—C8	124.8 (3)
C6—C1—C7	118.8 (3)	C9—C10—C11	119.8 (4)
C2—C1—C7	122.1 (3)	C9—C10—H10	120.1
O1—C2—C3	119.6 (3)	C11—C10—H10	120.1
O1—C2—C1	121.2 (3)	C12—C11—C10	117.6 (4)
C3—C2—C1	119.2 (3)	C12—C11—H11	121.2
C4—C3—C2	120.7 (3)	C10—C11—H11	121.2
C4—C3—I1	119.6 (3)	N3—C12—C11	124.7 (4)
C2—C3—I1	119.7 (3)	N3—C12—H12	117.7
C3—C4—C5	120.0 (3)	C11—C12—H12	117.7
C3—C4—H4	120.0	N3—C13—C9	124.4 (4)
C5—C4—H4	120.0	N3—C13—H13	117.8
C6—C5—C4	120.6 (3)	C9—C13—H13	117.8
C6—C5—I2	119.8 (3)	C15—C14—H14A	109.5
C4—C5—I2	119.6 (3)	C15—C14—H14B	109.5
C5—C6—C1	120.5 (3)	H14A—C14—H14B	109.5
C5—C6—H6	119.8	C15—C14—H14C	109.5
C1—C6—H6	119.8	H14A—C14—H14C	109.5
N1—C7—C1	119.8 (3)	H14B—C14—H14C	109.5
N1—C7—H7	120.1	N4—C15—C14	179.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.584 (4)	147
N2—H2···N4	0.90 (1)	2.22 (2)	3.076 (5)	160 (4)

Experimental details

Crystal data
Chemical formula	C₁₃H₉I₂N₃O₂·C₂H₃N
M_r	534.09
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.1347 (13), 13.3721 (16), 11.9999 (15)
β (°)	104.083 (6)
V (Å³)	1733.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.64
Crystal size (mm)	0.23 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.488, 0.529
No. of measured, independent and observed [I > 2σ(I)] reflections	10053, 3546, 2730
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.062, 1.01
No. of reflections	3546
No. of parameters	213
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.37

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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	1.86	2.584 (4)	147.1
N2—H2···N4	0.897 (10)	2.216 (19)	3.076 (5)	160 (4)

Acknowledgements

The authors acknowledge the Undergraduate Innovation Group Project of Zhejiang Province (project no. 2010R428015).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, S.-Y. & Wang, X. (2010a). Acta Cryst. E66, o1775. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, S.-Y. & Wang, X. (2010b). Acta Cryst. E66, o1805. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, S.-Y. & Wang, X.-L. (2011). Acta Cryst. E67, o1625. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, S.-Y. & You, Z. (2010a). Acta Cryst. E66, o1652. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Liu, S.-Y. & You, Z. (2010c). Acta Cryst. E66, o1662. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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(E)-N′-(2-Hy­dr­oxy-3,5-di­iodo­benzyl­­idene)nicotinohydrazide aceto­nitrile monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-N′-(2-Hydroxy-3,5-diiodobenzylidene)nicotinohydrazide acetonitrile monosolvate