N'-[(E)-2-Hy-droxy-3,5-diiodo-benzyl-idene]pyridine-3-carbohydrazide.

In the title compound, C(13)H(9)I(2)N(3)O(2), the dihedral angle between the two aromatic rings is 10.5 (2)°. The mol-ecule displays a trans configuration with respect to the C=N bond. An intra-molecular O-H⋯N hydrogen bond occurs. The crystal packing is stabilized by N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For the biological activity of isoniazid derivatives, see: Janin (2007 ▶); Kahwa et al. (1986 ▶); Chen et al. (1997 ▶); n class="Gene">Ren et al. (2002 ▶). For a related structure, see: Zhi & Wang (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H9I2N3O2

M = 493.03

Monoclinic,

a = 17.4800 (5) Å

b = 8.5710 (4) Å

c = 9.8650 (3) Å

β = 90.451 (4)°

V = 1477.94 (9) Å3

Z = 4

Mo Kα radiation

μ = 4.26 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.359, T max = 0.445

19735 measured reflections

4866 independent reflections

3640 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.106

S = 0.99

4866 reflections

183 parameters

H-atom parameters constrained

Δρmax = 1.68 e Å−3

Δρmin = −1.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103176X/bt5587sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103176X/bt5587Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103176X/bt5587Isup3.cml

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

C13H9I2N3O2	F(000) = 920
Mr = 493.03	Dx = 2.216 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4867 reflections
a = 17.4800 (5) Å	θ = 1.2–31.6°
b = 8.5710 (4) Å	µ = 4.26 mm−1
c = 9.8650 (3) Å	T = 293 K
β = 90.451 (4)°	Block, white
V = 1477.94 (9) Å3	0.25 × 0.22 × 0.19 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4866 independent reflections
Radiation source: fine-focus sealed tube	3640 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω and φ scans	θmax = 31.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −25→25
Tmin = 0.359, Tmax = 0.445	k = −12→12
19735 measured reflections	l = −14→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0525P)2 + 1.9568P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
4866 reflections	Δρmax = 1.68 e Å−3
183 parameters	Δρmin = −1.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (2)

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.

	x	y	z	Uiso*/Ueq
C1	0.28906 (18)	0.3439 (4)	0.7602 (3)	0.0383 (7)
H1	0.2713	0.2819	0.6892	0.046*
C2	0.36332 (17)	0.3990 (4)	0.7591 (3)	0.0364 (6)
C3	0.39014 (17)	0.4933 (4)	0.8622 (3)	0.0367 (6)
H3	0.4397	0.5328	0.8598	0.044*
C4	0.34258 (17)	0.5285 (4)	0.9691 (3)	0.0371 (6)
C5	0.26788 (16)	0.4720 (4)	0.9750 (3)	0.0347 (6)
C6	0.24076 (16)	0.3806 (4)	0.8670 (3)	0.0343 (6)
C7	0.16298 (17)	0.3211 (4)	0.8627 (3)	0.0381 (7)
H7	0.1459	0.2645	0.7880	0.046*
C8	0.00141 (15)	0.2795 (4)	1.0619 (3)	0.0347 (6)
C9	−0.07420 (15)	0.2011 (4)	1.0435 (3)	0.0338 (6)
C10	−0.13285 (18)	0.2377 (5)	1.1314 (4)	0.0491 (9)
H10	−0.1259	0.3125	1.1987	0.059*
C11	−0.2021 (2)	0.1607 (5)	1.1169 (4)	0.0559 (10)
H11	−0.2425	0.1819	1.1748	0.067*
C12	−0.2097 (2)	0.0528 (5)	1.0153 (4)	0.0548 (9)
H12	−0.2569	0.0043	1.0046	0.066*
C13	−0.08758 (17)	0.0874 (4)	0.9470 (3)	0.0419 (7)
H13	−0.0477	0.0612	0.8894	0.050*
N1	0.11794 (15)	0.3469 (3)	0.9622 (3)	0.0394 (6)
N2	0.04524 (14)	0.2851 (4)	0.9506 (3)	0.0385 (6)
H2	0.0284	0.2511	0.8740	0.046*
N3	−0.15404 (18)	0.0128 (4)	0.9311 (4)	0.0546 (8)
O1	0.22488 (13)	0.5069 (3)	1.0828 (2)	0.0458 (6)
H1A	0.1816	0.4722	1.0714	0.069*
O2	0.02167 (13)	0.3328 (3)	1.1712 (2)	0.0481 (6)
I1	0.434960 (14)	0.34479 (3)	0.59728 (3)	0.05286 (10)
I2	0.385470 (15)	0.66245 (4)	1.12850 (3)	0.06771 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0354 (14)	0.0453 (18)	0.0344 (15)	−0.0064 (12)	0.0072 (11)	−0.0015 (12)
C2	0.0329 (13)	0.0427 (17)	0.0336 (14)	−0.0020 (12)	0.0085 (11)	0.0027 (12)
C3	0.0273 (12)	0.0402 (17)	0.0425 (16)	−0.0042 (11)	0.0051 (11)	0.0005 (13)
C4	0.0312 (13)	0.0416 (17)	0.0384 (15)	−0.0028 (11)	0.0036 (11)	−0.0044 (12)
C5	0.0301 (12)	0.0424 (17)	0.0318 (14)	−0.0012 (11)	0.0050 (10)	0.0014 (12)
C6	0.0268 (12)	0.0439 (17)	0.0324 (14)	−0.0055 (11)	0.0042 (10)	0.0026 (12)
C7	0.0304 (13)	0.0504 (19)	0.0336 (14)	−0.0077 (12)	0.0035 (11)	−0.0011 (13)
C8	0.0278 (12)	0.0457 (17)	0.0306 (13)	−0.0019 (11)	0.0026 (10)	0.0022 (12)
C9	0.0260 (12)	0.0463 (16)	0.0291 (13)	−0.0010 (11)	0.0023 (10)	0.0072 (12)
C10	0.0318 (14)	0.075 (3)	0.0405 (17)	−0.0020 (15)	0.0078 (12)	−0.0049 (17)
C11	0.0305 (15)	0.083 (3)	0.054 (2)	−0.0024 (16)	0.0129 (14)	0.0105 (19)
C12	0.0334 (16)	0.065 (2)	0.066 (2)	−0.0117 (15)	0.0036 (15)	0.010 (2)
C13	0.0314 (14)	0.053 (2)	0.0412 (17)	−0.0026 (13)	0.0049 (12)	0.0016 (14)
N1	0.0289 (11)	0.0539 (17)	0.0354 (13)	−0.0087 (10)	0.0033 (10)	0.0044 (11)
N2	0.0276 (11)	0.0598 (17)	0.0280 (11)	−0.0081 (11)	0.0039 (9)	0.0021 (11)
N3	0.0393 (15)	0.060 (2)	0.065 (2)	−0.0134 (13)	0.0004 (14)	−0.0036 (16)
O1	0.0350 (11)	0.0663 (17)	0.0363 (12)	−0.0061 (10)	0.0104 (9)	−0.0084 (11)
O2	0.0360 (11)	0.0756 (19)	0.0326 (12)	−0.0084 (11)	0.0010 (9)	−0.0064 (11)
I1	0.04408 (14)	0.06674 (19)	0.04806 (15)	−0.00641 (10)	0.01933 (10)	−0.00998 (11)
I2	0.04370 (14)	0.0942 (3)	0.06543 (19)	−0.02088 (13)	0.00969 (12)	−0.03975 (15)

C1—C2	1.382 (4)	C8—N2	1.344 (4)
C1—C6	1.391 (4)	C8—C9	1.492 (4)
C1—H1	0.9300	C9—C13	1.381 (5)
C2—C3	1.378 (4)	C9—C10	1.384 (4)
C2—I1	2.089 (3)	C10—C11	1.385 (5)
C3—C4	1.381 (4)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.369 (6)
C4—C5	1.394 (4)	C11—H11	0.9300
C4—I2	2.082 (3)	C12—N3	1.329 (5)
C5—O1	1.341 (4)	C12—H12	0.9300
C5—C6	1.402 (4)	C13—N3	1.334 (4)
C6—C7	1.452 (4)	C13—H13	0.9300
C7—N1	1.282 (4)	N1—N2	1.381 (3)
C7—H7	0.9300	N2—H2	0.8600
C8—O2	1.221 (4)	O1—H1A	0.8200
C2—C1—C6	120.3 (3)	N2—C8—C9	115.3 (3)
C2—C1—H1	119.9	C13—C9—C10	118.0 (3)
C6—C1—H1	119.9	C13—C9—C8	123.1 (3)
C1—C2—C3	120.6 (3)	C10—C9—C8	118.8 (3)
C1—C2—I1	119.9 (2)	C11—C10—C9	118.6 (4)
C3—C2—I1	119.5 (2)	C11—C10—H10	120.7
C4—C3—C2	119.2 (3)	C9—C10—H10	120.7
C4—C3—H3	120.4	C12—C11—C10	118.5 (3)
C2—C3—H3	120.4	C12—C11—H11	120.7
C3—C4—C5	121.7 (3)	C10—C11—H11	120.7
C3—C4—I2	118.8 (2)	N3—C12—C11	124.3 (3)
C5—C4—I2	119.5 (2)	N3—C12—H12	117.8
O1—C5—C4	119.1 (3)	C11—C12—H12	117.8
O1—C5—C6	122.6 (3)	N3—C13—C9	124.2 (3)
C4—C5—C6	118.3 (3)	N3—C13—H13	117.9
C1—C6—C5	119.9 (3)	C9—C13—H13	117.9
C1—C6—C7	118.2 (3)	C7—N1—N2	116.2 (3)
C5—C6—C7	121.9 (3)	C8—N2—N1	118.5 (3)
N1—C7—C6	119.8 (3)	C8—N2—H2	120.8
N1—C7—H7	120.1	N1—N2—H2	120.8
C6—C7—H7	120.1	C12—N3—C13	116.4 (3)
O2—C8—N2	123.0 (3)	C5—O1—H1A	109.5
O2—C8—C9	121.8 (3)
C6—C1—C2—C3	−1.2 (5)	C5—C6—C7—N1	−2.7 (5)
C6—C1—C2—I1	−179.4 (2)	O2—C8—C9—C13	−152.5 (3)
C1—C2—C3—C4	1.9 (5)	N2—C8—C9—C13	26.8 (5)
I1—C2—C3—C4	−179.8 (2)	O2—C8—C9—C10	24.1 (5)
C2—C3—C4—C5	−0.5 (5)	N2—C8—C9—C10	−156.6 (3)
C2—C3—C4—I2	177.2 (2)	C13—C9—C10—C11	−1.0 (5)
C3—C4—C5—O1	178.5 (3)	C8—C9—C10—C11	−177.8 (3)
I2—C4—C5—O1	0.8 (4)	C9—C10—C11—C12	−0.6 (6)
C3—C4—C5—C6	−1.6 (5)	C10—C11—C12—N3	2.1 (7)
I2—C4—C5—C6	−179.3 (2)	C10—C9—C13—N3	1.5 (5)
C2—C1—C6—C5	−1.0 (5)	C8—C9—C13—N3	178.1 (3)
C2—C1—C6—C7	179.4 (3)	C6—C7—N1—N2	−179.4 (3)
O1—C5—C6—C1	−177.7 (3)	O2—C8—N2—N1	3.4 (5)
C4—C5—C6—C1	2.3 (5)	C9—C8—N2—N1	−175.9 (3)
O1—C5—C6—C7	1.9 (5)	C7—N1—N2—C8	166.1 (3)
C4—C5—C6—C7	−178.0 (3)	C11—C12—N3—C13	−1.7 (6)
C1—C6—C7—N1	177.0 (3)	C9—C13—N3—C12	−0.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.88	2.599 (4)	146
N2—H2···O2i	0.86	2.13	2.962 (4)	163.
C7—H7···O2i	0.93	2.59	3.367 (4)	142.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.88	2.599 (4)	146
N2—H2⋯O2i	0.86	2.13	2.962 (4)	163
C7—H7⋯O2i	0.93	2.59	3.367 (4)	142

Symmetry code: (i) .