(E)-2-(2-Hy-droxy-5-iodo-benzyl-idene)hydrazinecarboxamide.

In the title mol-ecule, C(8)H(8)IN(3)O(2), there is an intra-molecular O-H⋯N hydrogen bond between the hy-droxy group and the imine N atom, which generates an S(6) ring. In the crystal, the carbonyl O atom accepts two different N-H⋯O hydrogen bonds, which connect mol-ecules with two R(2) (2)(8) motifs.

Related literature

For historical background to semicarbazones, see: Arapov et al. (1987 ▶); Pickart et al. (1983 ▶). For related structures see: Bikas et al. (2010 ▶, 2012a ▶,b ▶); Monfared et al. (2010a ▶). For background to the development of hydrazide derivatives for biological evaluation, see: Carvalho et al. (2008 ▶). For catalytic applications of aroylhydrazones, see: Monfared et al. (2010b ▶). For a similiar structure, see: Abboud et al. (1995 ▶).

Experimental

Crystal data

C8H8IN3O2

M = 305.07

Monoclinic,

a = 9.1066 (18) Å

b = 7.6277 (15) Å

c = 14.375 (3) Å

β = 95.31 (3)°

V = 994.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.20 mm−1

T = 120 K

0.25 × 0.13 × 0.12 mm

Data collection

Stoe IPDS 2T diffractometer

Absorption correction: numerical (shape of crystal determined optically; X-RED32 and X-SHAPE, Stoe & Cie, 2005 ▶) T min = 0.502, T max = 0.700

10438 measured reflections

2686 independent reflections

2362 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.056

S = 1.13

2686 reflections

143 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.75 e Å−3

Δρmin = −0.71 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010197/vm2154sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010197/vm2154Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010197/vm2154Isup3.cml

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

C8H8IN3O2	F(000) = 584
Mr = 305.07	Dx = 2.038 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 2686 reflections
a = 9.1066 (18) Å	θ = 2.7–29.2°
b = 7.6277 (15) Å	µ = 3.20 mm−1
c = 14.375 (3) Å	T = 120 K
β = 95.31 (3)°	Block, colorless
V = 994.3 (3) Å3	0.25 × 0.13 × 0.12 mm
Z = 4

Stoe IPDS 2T diffractometer	2686 independent reflections
Radiation source: fine-focus sealed tube	2362 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 0.15 mm pixels mm-1	θmax = 29.2°, θmin = 2.7°
rotation method scans	h = −12→12
Absorption correction: numerical (shape of crystal determined optically; X-RED32 and X-SHAPE, Stoe & Cie, 2005)	k = −10→10
Tmin = 0.502, Tmax = 0.700	l = −18→19
10438 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0208P)2 + 1.0932P] where P = (Fo2 + 2Fc2)/3
2686 reflections	(Δ/σ)max = 0.001
143 parameters	Δρmax = 0.75 e Å−3
1 restraint	Δρmin = −0.71 e Å−3

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
I1	0.71642 (2)	0.52615 (2)	1.210107 (13)	0.02620 (6)
O2	1.52011 (18)	1.0591 (2)	0.88088 (11)	0.0160 (3)
N2	1.3349 (2)	0.9116 (3)	0.93933 (14)	0.0149 (4)
C8	1.3955 (2)	0.9896 (3)	0.86612 (16)	0.0137 (4)
N3	1.3205 (2)	0.9864 (3)	0.78198 (15)	0.0166 (4)
N1	1.1902 (2)	0.8602 (3)	0.93061 (14)	0.0134 (4)
O1	0.9242 (2)	0.8354 (3)	0.84348 (13)	0.0217 (4)
C1	0.9856 (3)	0.7452 (3)	1.00333 (17)	0.0139 (4)
C2	0.8840 (3)	0.7661 (3)	0.92413 (17)	0.0150 (4)
C7	1.1398 (3)	0.7979 (3)	1.00415 (16)	0.0137 (4)
H7	1.2036	0.7860	1.0599	0.016*
C6	0.9357 (3)	0.6755 (3)	1.08517 (17)	0.0165 (5)
H6	1.0028	0.6609	1.1393	0.020*
C4	0.6899 (3)	0.6494 (3)	1.00927 (19)	0.0191 (5)
H4	0.5895	0.6172	1.0115	0.023*
C3	0.7373 (3)	0.7178 (3)	0.92780 (18)	0.0187 (5)
H3	0.6691	0.7319	0.8742	0.022*
C5	0.7893 (3)	0.6278 (3)	1.08752 (18)	0.0173 (5)
H2	1.380 (4)	0.917 (4)	0.990 (3)	0.022 (8)*
H3A	1.244 (4)	0.929 (5)	0.773 (3)	0.029 (9)*
H3B	1.359 (4)	1.028 (5)	0.738 (3)	0.028 (9)*
H1	1.016 (2)	0.849 (5)	0.849 (3)	0.037 (10)*

	U11	U22	U33	U12	U13	U23
I1	0.03341 (10)	0.02256 (9)	0.02507 (9)	−0.00405 (7)	0.01569 (7)	0.00293 (7)
O2	0.0139 (7)	0.0241 (10)	0.0102 (8)	−0.0040 (6)	0.0015 (6)	−0.0006 (6)
N2	0.0121 (9)	0.0243 (10)	0.0081 (9)	−0.0052 (8)	0.0003 (7)	0.0002 (8)
C8	0.0143 (9)	0.0174 (12)	0.0095 (9)	0.0005 (8)	0.0019 (8)	−0.0004 (8)
N3	0.0153 (9)	0.0243 (11)	0.0101 (9)	−0.0040 (8)	0.0007 (7)	0.0005 (8)
N1	0.0112 (9)	0.0159 (9)	0.0132 (9)	−0.0012 (7)	0.0011 (7)	−0.0023 (7)
O1	0.0150 (9)	0.0375 (11)	0.0121 (8)	−0.0015 (7)	−0.0009 (7)	0.0058 (7)
C1	0.0149 (11)	0.0130 (12)	0.0141 (10)	−0.0002 (8)	0.0032 (8)	−0.0014 (8)
C2	0.0147 (11)	0.0174 (11)	0.0131 (11)	−0.0005 (8)	0.0020 (8)	−0.0005 (9)
C7	0.0130 (10)	0.0171 (11)	0.0109 (10)	−0.0006 (8)	0.0010 (8)	−0.0011 (8)
C6	0.0176 (11)	0.0180 (12)	0.0140 (11)	0.0003 (9)	0.0030 (9)	0.0010 (9)
C4	0.0147 (11)	0.0188 (12)	0.0249 (13)	−0.0037 (9)	0.0070 (9)	−0.0054 (10)
C3	0.0149 (11)	0.0231 (13)	0.0181 (12)	0.0001 (9)	0.0017 (9)	−0.0031 (9)
C5	0.0204 (11)	0.0137 (11)	0.0194 (12)	−0.0014 (8)	0.0106 (9)	0.0005 (9)

I1—C5	2.089 (2)	C1—C6	1.404 (3)
O2—C8	1.253 (3)	C1—C2	1.408 (3)
N2—C8	1.369 (3)	C1—C7	1.460 (3)
N2—N1	1.369 (3)	C2—C3	1.391 (3)
N2—H2	0.80 (4)	C7—H7	0.9500
C8—N3	1.333 (3)	C6—C5	1.385 (3)
N3—H3A	0.82 (4)	C6—H6	0.9500
N3—H3B	0.81 (4)	C4—C5	1.387 (4)
N1—C7	1.282 (3)	C4—C3	1.387 (4)
O1—C2	1.355 (3)	C4—H4	0.9500
O1—H1	0.841 (18)	C3—H3	0.9500
C8—N2—N1	120.5 (2)	C3—C2—C1	120.0 (2)
C8—N2—H2	118 (2)	N1—C7—C1	120.9 (2)
N1—N2—H2	120 (2)	N1—C7—H7	119.6
O2—C8—N3	122.8 (2)	C1—C7—H7	119.6
O2—C8—N2	118.5 (2)	C5—C6—C1	120.4 (2)
N3—C8—N2	118.7 (2)	C5—C6—H6	119.8
C8—N3—H3A	121 (3)	C1—C6—H6	119.8
C8—N3—H3B	118 (3)	C5—C4—C3	119.9 (2)
H3A—N3—H3B	120 (4)	C5—C4—H4	120.0
C7—N1—N2	116.5 (2)	C3—C4—H4	120.0
C2—O1—H1	108 (3)	C4—C3—C2	120.4 (2)
C6—C1—C2	118.8 (2)	C4—C3—H3	119.8
C6—C1—C7	118.9 (2)	C2—C3—H3	119.8
C2—C1—C7	122.3 (2)	C6—C5—C4	120.4 (2)
O1—C2—C3	118.2 (2)	C6—C5—I1	120.0 (2)
O1—C2—C1	121.8 (2)	C4—C5—I1	119.59 (17)
N1—N2—C8—O2	169.1 (2)	C2—C1—C6—C5	0.2 (4)
N1—N2—C8—N3	−11.9 (3)	C7—C1—C6—C5	178.5 (2)
C8—N2—N1—C7	−175.9 (2)	C5—C4—C3—C2	−0.3 (4)
C6—C1—C2—O1	178.8 (2)	O1—C2—C3—C4	−178.8 (2)
C7—C1—C2—O1	0.6 (4)	C1—C2—C3—C4	0.1 (4)
C6—C1—C2—C3	−0.1 (4)	C1—C6—C5—C4	−0.4 (4)
C7—C1—C2—C3	−178.3 (2)	C1—C6—C5—I1	−179.51 (18)
N2—N1—C7—C1	177.8 (2)	C3—C4—C5—C6	0.5 (4)
C6—C1—C7—N1	179.1 (2)	C3—C4—C5—I1	179.59 (19)
C2—C1—C7—N1	−2.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O2i	0.81 (4)	2.13 (4)	2.920 (3)	163 (3)
N2—H2···O2ii	0.80 (4)	2.00 (4)	2.800 (3)	176 (3)
O1—H1···N1	0.84 (2)	1.88 (3)	2.628 (3)	147 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O2i	0.81 (4)	2.13 (4)	2.920 (3)	163 (3)
N2—H2⋯O2ii	0.80 (4)	2.00 (4)	2.800 (3)	176 (3)
O1—H1⋯N1	0.84 (2)	1.88 (3)	2.628 (3)	147 (4)

Symmetry codes: (i) ; (ii) .