(E)-N'-(2-Hy-droxy-3,5-diiodo-benzyl-idene)nicotinohydrazide acetonitrile monosolvate.

In the hydrazone molecule of the title compound, C(13)H(9)I(2)N(3)O(2)·CH(3)CN, the aromatic rings form a dihedral angle of 9.4 (3)°. In the crystal structure, inter-molecular I⋯N inter-actions [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 = 534.09

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.062

S = 1.01

3546 reflections

213 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.37 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020770/cv5102sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811020770/cv5102Isup3.cml

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

C13H9I2N3O2·C2H3N	F(000) = 1008
Mr = 534.09	Dx = 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

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

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(Fo2) + (0.0273P)2] where P = (Fo2 + 2Fc2)/3
3546 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 0.41 e Å−3
1 restraint	Δρmin = −0.37 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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)