4-Iodo-benzohydrazide.

In the structure of the title compound, C(7)H(7)IN(2)O, the hydrazide group is inclined at 13.3 (3)° with respect to the benzene ring. The structure is stabilized by inter-molecular N-H⋯N and N-H⋯O hydrogen bonds involving the hydrazide group, resulting in six- and ten-membered rings with R(2) (2)(6) and R(2) (2)(10) graph-set notations, respectively.

Related literature

For related structures, see: Kallel et al. (1992 ▶); Saraogi et al. (2002 ▶); Ashiq, Jamal et al. (2008 ▶). For related literature, see: n class="Gene">Ara et al. (2007 ▶); Ashiq, Ara et al. (2008 ▶); Bernstein et al. (1994 ▶).

Experimental

Crystal data

C7H7IN2O

M = 262.05

Monoclinic,

a = 28.4394 (18) Å

b = 4.4514 (3) Å

c = 13.3216 (9) Å

β = 94.292 (2)°

V = 1681.72 (19) Å3

Z = 8

Mo Kα radiation

μ = 3.76 mm−1

T = 296 (2) K

0.12 × 0.08 × 0.06 mm

Data collection

Bruker KappaAPEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.581, T max = 0.806

9236 measured reflections

2069 independent reflections

1645 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.106

S = 1.05

2069 reflections

109 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −1.33 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: n class="Gene">APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033898/pv2109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033898/pv2109Isup2.hkl

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

C7H7IN2O	F(000) = 992
Mr = 262.05	Dx = 2.072 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3495 reflections
a = 28.4394 (18) Å	θ = 1.4–28.3°
b = 4.4514 (3) Å	µ = 3.76 mm−1
c = 13.3216 (9) Å	T = 296 K
β = 94.292 (2)°	Needle, colorless
V = 1681.72 (19) Å3	0.12 × 0.08 × 0.06 mm
Z = 8

Bruker KappaAPEXII CCD diffractometer	2069 independent reflections
Radiation source: fine-focus sealed tube	1645 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −37→37
Tmin = 0.581, Tmax = 0.806	k = −5→5
9236 measured reflections	l = −17→17

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) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0565P)2 + 5.77P] where P = (Fo2 + 2Fc2)/3
2069 reflections	(Δ/σ)max = 0.001
109 parameters	Δρmax = 0.55 e Å−3
3 restraints	Δρmin = −1.32 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 > 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	0.215538 (11)	1.09655 (7)	0.64904 (2)	0.05339 (15)
O1	0.05919 (14)	0.3811 (8)	0.2873 (2)	0.0582 (10)
N1	0.03174 (13)	0.1851 (9)	0.4262 (2)	0.0404 (8)
H1A	0.0321 (18)	0.170 (11)	0.4905 (9)	0.049*
N2	−0.00239 (14)	0.0017 (10)	0.3743 (2)	0.0408 (8)
H2A	−0.0195 (16)	0.119 (9)	0.335 (3)	0.049*
H2B	0.0127 (17)	−0.126 (9)	0.341 (3)	0.049*
C1	0.09627 (14)	0.5363 (10)	0.4445 (3)	0.0358 (8)
C2	0.09382 (15)	0.5693 (10)	0.5484 (3)	0.0403 (9)
H2	0.0695	0.4777	0.5799	0.048*
C3	0.12697 (15)	0.7356 (11)	0.6046 (3)	0.0441 (10)
H3	0.1244	0.7611	0.6733	0.053*
C4	0.16380 (15)	0.8638 (9)	0.5594 (3)	0.0397 (9)
C5	0.16696 (17)	0.8370 (11)	0.4566 (3)	0.0489 (11)
H5	0.1918	0.9256	0.4260	0.059*
C6	0.13267 (18)	0.6768 (12)	0.3998 (3)	0.0489 (11)
H6	0.1342	0.6637	0.3305	0.059*
C7	0.06129 (16)	0.3608 (9)	0.3801 (3)	0.0375 (9)

	U11	U22	U33	U12	U13	U23
I1	0.0461 (2)	0.0498 (2)	0.0626 (2)	−0.00097 (13)	−0.00736 (14)	0.00125 (13)
O1	0.069 (2)	0.080 (3)	0.0273 (13)	−0.0221 (19)	0.0124 (14)	−0.0003 (14)
N1	0.0469 (19)	0.0465 (19)	0.0277 (14)	−0.0046 (17)	0.0010 (13)	0.0067 (14)
N2	0.050 (2)	0.0425 (19)	0.0302 (15)	0.0003 (17)	0.0039 (14)	0.0051 (15)
C1	0.0384 (19)	0.038 (2)	0.0317 (17)	0.0053 (17)	0.0080 (14)	0.0015 (16)
C2	0.039 (2)	0.051 (3)	0.0317 (17)	−0.0001 (18)	0.0109 (15)	0.0041 (17)
C3	0.043 (2)	0.054 (3)	0.0352 (18)	0.001 (2)	0.0049 (16)	0.0000 (19)
C4	0.036 (2)	0.039 (2)	0.044 (2)	0.0035 (16)	−0.0004 (16)	0.0018 (17)
C5	0.048 (2)	0.053 (3)	0.047 (2)	−0.008 (2)	0.0168 (19)	0.002 (2)
C6	0.055 (3)	0.056 (3)	0.038 (2)	−0.004 (2)	0.0156 (19)	0.001 (2)
C7	0.042 (2)	0.041 (2)	0.0309 (17)	0.0060 (17)	0.0088 (15)	0.0037 (15)

I1—C4	2.098 (4)	C1—C7	1.486 (6)
O1—C7	1.237 (5)	C2—C3	1.375 (6)
N1—C7	1.332 (5)	C2—H2	0.9300
N1—N2	1.410 (6)	C3—C4	1.371 (6)
N1—H1A	0.857 (10)	C3—H3	0.9300
N2—H2A	0.862 (10)	C4—C5	1.384 (6)
N2—H2B	0.860 (10)	C5—C6	1.386 (7)
C1—C6	1.382 (6)	C5—H5	0.9300
C1—C2	1.398 (5)	C6—H6	0.9300
C7—N1—N2	123.3 (3)	C2—C3—H3	120.0
C7—N1—H1A	123 (3)	C3—C4—C5	120.5 (4)
N2—N1—H1A	114 (3)	C3—C4—I1	118.8 (3)
N1—N2—H2A	106 (3)	C5—C4—I1	120.7 (3)
N1—N2—H2B	107 (4)	C4—C5—C6	119.3 (4)
H2A—N2—H2B	112 (5)	C4—C5—H5	120.4
C6—C1—C2	118.3 (4)	C6—C5—H5	120.4
C6—C1—C7	118.6 (3)	C1—C6—C5	121.1 (4)
C2—C1—C7	123.1 (4)	C1—C6—H6	119.5
C3—C2—C1	120.8 (4)	C5—C6—H6	119.5
C3—C2—H2	119.6	O1—C7—N1	121.3 (4)
C1—C2—H2	119.6	O1—C7—C1	121.3 (4)
C4—C3—C2	120.0 (4)	N1—C7—C1	117.4 (3)
C4—C3—H3	120.0
C6—C1—C2—C3	−0.5 (7)	C7—C1—C6—C5	−178.3 (4)
C7—C1—C2—C3	−179.6 (4)	C4—C5—C6—C1	−1.9 (8)
C1—C2—C3—C4	−2.0 (7)	N2—N1—C7—O1	2.7 (7)
C2—C3—C4—C5	2.5 (7)	N2—N1—C7—C1	−178.5 (4)
C2—C3—C4—I1	−176.8 (3)	C6—C1—C7—O1	−12.8 (6)
C3—C4—C5—C6	−0.6 (7)	C2—C1—C7—O1	166.3 (4)
I1—C4—C5—C6	178.8 (4)	C6—C1—C7—N1	168.4 (4)
C2—C1—C6—C5	2.4 (7)	C2—C1—C7—N1	−12.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.86 (1)	2.19 (3)	2.964 (5)	151 (5)
N2—H2A···O1ii	0.86 (1)	2.24 (1)	3.094 (5)	170 (5)
C3—H3···O1iii	0.93	2.56	3.257 (5)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.857 (10)	2.19 (3)	2.964 (5)	151 (5)
N2—H2A⋯O1ii	0.862 (10)	2.240 (14)	3.094 (5)	170 (5)
C3—H3⋯O1iii	0.93	2.56	3.257 (5)	132

Symmetry codes: (i) ; (ii) ; (iii) .