N'-[(E)-2-Hy-droxy-5-iodo-benzyl-idene]-4-methyl-benzene-sulfono-hydrazide.

In the title mol-ecule, C(14)H(13)IN(2)O(3)S, the dihedral angle between the planes of the benzene and toluene rings is 84.3 (3)°. The mol-ecule displays a trans conformation with respect to the C=N bond. There is an intra-molecular O-H⋯N hydrogen bond with the azomethine N atom as acceptor. In the crystal, N-H⋯O hydrogen bonds connect the mol-ecules into chains running along the b axis.

Related literature

For background to sulfonamides, see: Kayser et al. (2004 ▶). For related structures and their applications, see: Shahverdizadeh et al. (2011 ▶); Ali et al. (2007 ▶); Tierney et al. (2006 ▶); Silva et al. (2006 ▶). For polymorphism in sulfono­hydrazides, see: Kia et al. (2008 ▶); Tai et al. (2009 ▶).

Experimental

Crystal data

C14H13IN2O3S

M = 416.23

Monoclinic,

a = 6.2467 (12) Å

b = 10.394 (2) Å

c = 11.971 (2) Å

β = 92.42 (3)°

V = 776.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.21 mm−1

T = 298 K

0.50 × 0.40 × 0.20 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005 ▶) T min = 0.405, T max = 0.667

6035 measured reflections

3841 independent reflections

2791 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.114

S = 0.92

3841 reflections

197 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.88 e Å−3

Δρmin = −0.99 e Å−3

Absolute structure: Flack (1983 ▶), 1641 Friedel pairs

Flack parameter: −0.06 (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/S1600536812035738/bt5993sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035738/bt5993Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035738/bt5993Isup3.cml

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

C14H13IN2O3S	F(000) = 408
Mr = 416.23	Dx = 1.780 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3841 reflections
a = 6.2467 (12) Å	θ = 1.7–29.2°
b = 10.394 (2) Å	µ = 2.21 mm−1
c = 11.971 (2) Å	T = 298 K
β = 92.42 (3)°	Plate, colorless
V = 776.6 (3) Å3	0.50 × 0.40 × 0.20 mm
Z = 2

Stoe IPDS 2 diffractometer	3841 independent reflections
Radiation source: fine-focus sealed tube	2791 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Detector resolution: 0.15 mm pixels mm-1	θmax = 29.2°, θmin = 1.7°
rotation method scans	h = −7→8
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	k = −14→13
Tmin = 0.405, Tmax = 0.667	l = −16→16
6035 measured reflections

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.071P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max < 0.001
3841 reflections	Δρmax = 0.88 e Å−3
197 parameters	Δρmin = −0.99 e Å−3
3 restraints	Absolute structure: Flack (1983), 1641 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.06 (3)

Experimental. shape of crystal determined optically

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	0.80088 (6)	0.64270 (4)	−0.32973 (4)	0.07048 (17)
S1	−0.2369 (2)	0.51804 (13)	0.17826 (10)	0.0423 (3)
O1	0.2908 (7)	0.3287 (4)	0.0117 (4)	0.0493 (9)
O2	−0.1752 (7)	0.3869 (4)	0.1850 (4)	0.0584 (11)
O3	−0.4564 (6)	0.5561 (4)	0.1806 (4)	0.0566 (10)
N1	0.0354 (7)	0.5237 (4)	0.0251 (3)	0.0387 (9)
N2	−0.1570 (7)	0.5714 (4)	0.0580 (4)	0.0427 (10)
C1	0.6247 (8)	0.5391 (5)	−0.2153 (4)	0.0437 (12)
C2	0.6906 (8)	0.4168 (6)	−0.1848 (4)	0.0452 (12)
H2	0.8103	0.3806	−0.2161	0.054*
C3	0.5781 (9)	0.3485 (5)	−0.1074 (5)	0.0455 (12)
H3	0.6245	0.2672	−0.0849	0.055*
C4	0.3963 (8)	0.4012 (5)	−0.0633 (4)	0.0377 (10)
C5	0.3257 (8)	0.5256 (5)	−0.0950 (4)	0.0369 (10)
C6	0.4431 (8)	0.5934 (5)	−0.1716 (4)	0.0406 (11)
H6	0.3999	0.6755	−0.1937	0.049*
C7	0.1345 (8)	0.5822 (5)	−0.0518 (4)	0.0374 (10)
H7	0.0837	0.6605	−0.0795	0.045*
C8	−0.0891 (8)	0.6054 (5)	0.2828 (4)	0.0420 (12)
C9	−0.1739 (10)	0.7173 (5)	0.3242 (5)	0.0456 (12)
H9	−0.3088	0.7457	0.2992	0.055*
C10	−0.0552 (11)	0.7865 (6)	0.4035 (5)	0.0543 (15)
H10	−0.1116	0.8620	0.4317	0.065*
C11	0.1458 (11)	0.7461 (6)	0.4418 (5)	0.0543 (14)
C12	0.2764 (15)	0.8255 (10)	0.5268 (7)	0.082 (2)
H12A	0.2910	0.7791	0.5960	0.123*
H12B	0.2049	0.9058	0.5390	0.123*
H12C	0.4158	0.8419	0.4991	0.123*
C13	0.2264 (9)	0.6346 (9)	0.3970 (5)	0.0598 (14)
H13	0.3618	0.6065	0.4214	0.072*
C14	0.1134 (10)	0.5641 (6)	0.3177 (5)	0.0532 (14)
H14	0.1717	0.4899	0.2880	0.064*
H1	0.173 (6)	0.359 (7)	0.024 (6)	0.064*
H2A	−0.186 (11)	0.649 (3)	0.037 (6)	0.064*

	U11	U22	U33	U12	U13	U23
I1	0.0614 (2)	0.0783 (3)	0.0737 (3)	−0.0046 (3)	0.02653 (18)	0.0203 (3)
S1	0.0421 (7)	0.0388 (6)	0.0469 (6)	−0.0040 (5)	0.0134 (5)	−0.0008 (5)
O1	0.057 (2)	0.0328 (19)	0.060 (2)	0.0003 (17)	0.019 (2)	0.0067 (16)
O2	0.070 (3)	0.042 (2)	0.064 (3)	−0.007 (2)	0.012 (2)	0.0030 (18)
O3	0.040 (2)	0.063 (2)	0.068 (2)	−0.0066 (18)	0.0153 (18)	−0.008 (2)
N1	0.041 (2)	0.036 (2)	0.040 (2)	0.0023 (18)	0.0073 (17)	−0.0028 (17)
N2	0.044 (2)	0.041 (2)	0.044 (2)	0.002 (2)	0.0133 (19)	−0.0004 (19)
C1	0.042 (3)	0.050 (3)	0.039 (2)	−0.008 (2)	0.008 (2)	0.001 (2)
C2	0.038 (3)	0.047 (3)	0.050 (3)	0.002 (2)	0.007 (2)	−0.008 (2)
C3	0.044 (3)	0.037 (3)	0.056 (3)	0.004 (2)	0.007 (2)	−0.004 (2)
C4	0.042 (3)	0.030 (2)	0.041 (2)	−0.005 (2)	0.005 (2)	−0.0026 (19)
C5	0.038 (2)	0.037 (3)	0.035 (2)	−0.006 (2)	0.0018 (19)	−0.002 (2)
C6	0.045 (3)	0.035 (2)	0.042 (2)	0.002 (2)	0.005 (2)	0.0055 (19)
C7	0.043 (3)	0.029 (2)	0.041 (2)	0.001 (2)	0.004 (2)	−0.0008 (18)
C8	0.039 (3)	0.044 (3)	0.044 (2)	−0.004 (2)	0.015 (2)	0.0020 (19)
C9	0.046 (3)	0.043 (3)	0.048 (3)	0.004 (2)	0.005 (2)	0.004 (2)
C10	0.067 (4)	0.047 (3)	0.051 (3)	0.002 (3)	0.018 (3)	−0.007 (2)
C11	0.060 (4)	0.064 (4)	0.040 (3)	−0.014 (3)	0.011 (2)	0.001 (3)
C12	0.086 (6)	0.099 (6)	0.059 (4)	0.000 (5)	−0.008 (4)	−0.013 (4)
C13	0.047 (3)	0.077 (4)	0.055 (3)	0.011 (4)	0.005 (2)	0.011 (4)
C14	0.050 (3)	0.052 (3)	0.059 (3)	0.007 (3)	0.013 (3)	−0.003 (3)

I1—C1	2.092 (5)	C5—C7	1.447 (7)
S1—O2	1.418 (5)	C6—H6	0.9300
S1—O3	1.429 (4)	C7—H7	0.9300
S1—N2	1.640 (4)	C8—C9	1.379 (7)
S1—C8	1.774 (5)	C8—C14	1.384 (8)
O1—C4	1.364 (6)	C9—C10	1.381 (9)
O1—H1	0.82 (2)	C9—H9	0.9300
N1—C7	1.283 (6)	C10—C11	1.384 (9)
N1—N2	1.373 (6)	C10—H10	0.9300
N2—H2A	0.86 (2)	C11—C13	1.380 (11)
C1—C2	1.380 (8)	C11—C12	1.521 (11)
C1—C6	1.389 (7)	C12—H12A	0.9600
C2—C3	1.382 (8)	C12—H12B	0.9600
C2—H2	0.9300	C12—H12C	0.9600
C3—C4	1.385 (7)	C13—C14	1.371 (10)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.413 (7)	C14—H14	0.9300
C5—C6	1.390 (6)
O2—S1—O3	121.6 (3)	C5—C6—H6	119.9
O2—S1—N2	106.4 (2)	N1—C7—C5	119.6 (4)
O3—S1—N2	104.6 (3)	N1—C7—H7	120.2
O2—S1—C8	108.7 (3)	C5—C7—H7	120.2
O3—S1—C8	108.4 (2)	C9—C8—C14	120.9 (5)
N2—S1—C8	106.1 (2)	C9—C8—S1	119.3 (4)
C4—O1—H1	111 (5)	C14—C8—S1	119.7 (4)
C7—N1—N2	119.3 (4)	C8—C9—C10	118.9 (6)
N1—N2—S1	115.6 (3)	C8—C9—H9	120.6
N1—N2—H2A	115 (5)	C10—C9—H9	120.6
S1—N2—H2A	120 (5)	C9—C10—C11	121.5 (6)
C2—C1—C6	120.9 (5)	C9—C10—H10	119.2
C2—C1—I1	119.2 (4)	C11—C10—H10	119.2
C6—C1—I1	119.8 (4)	C13—C11—C10	117.8 (6)
C1—C2—C3	119.7 (5)	C13—C11—C12	121.4 (7)
C1—C2—H2	120.1	C10—C11—C12	120.7 (7)
C3—C2—H2	120.1	C11—C12—H12A	109.5
C2—C3—C4	120.0 (5)	C11—C12—H12B	109.5
C2—C3—H3	120.0	H12A—C12—H12B	109.5
C4—C3—H3	120.0	C11—C12—H12C	109.5
O1—C4—C3	117.3 (5)	H12A—C12—H12C	109.5
O1—C4—C5	121.9 (4)	H12B—C12—H12C	109.5
C3—C4—C5	120.8 (5)	C14—C13—C11	122.1 (6)
C6—C5—C4	118.3 (4)	C14—C13—H13	118.9
C6—C5—C7	119.8 (5)	C11—C13—H13	118.9
C4—C5—C7	122.0 (4)	C13—C14—C8	118.7 (6)
C1—C6—C5	120.3 (5)	C13—C14—H14	120.6
C1—C6—H6	119.9	C8—C14—H14	120.6
C7—N1—N2—S1	−162.9 (4)	C6—C5—C7—N1	−174.8 (5)
O2—S1—N2—N1	−36.8 (5)	C4—C5—C7—N1	6.4 (7)
O3—S1—N2—N1	−166.7 (4)	O2—S1—C8—C9	−153.8 (4)
C8—S1—N2—N1	78.8 (4)	O3—S1—C8—C9	−19.8 (5)
C6—C1—C2—C3	−1.7 (8)	N2—S1—C8—C9	92.0 (4)
I1—C1—C2—C3	178.6 (4)	O2—S1—C8—C14	29.4 (5)
C1—C2—C3—C4	1.9 (8)	O3—S1—C8—C14	163.4 (4)
C2—C3—C4—O1	179.3 (5)	N2—S1—C8—C14	−84.8 (5)
C2—C3—C4—C5	−1.1 (8)	C14—C8—C9—C10	−1.5 (8)
O1—C4—C5—C6	179.7 (5)	S1—C8—C9—C10	−178.3 (4)
C3—C4—C5—C6	0.1 (7)	C8—C9—C10—C11	0.1 (8)
O1—C4—C5—C7	−1.5 (7)	C9—C10—C11—C13	0.9 (9)
C3—C4—C5—C7	179.0 (5)	C9—C10—C11—C12	178.4 (6)
C2—C1—C6—C5	0.7 (8)	C10—C11—C13—C14	−0.5 (9)
I1—C1—C6—C5	−179.6 (4)	C12—C11—C13—C14	−177.9 (7)
C4—C5—C6—C1	0.1 (7)	C11—C13—C14—C8	−0.9 (10)
C7—C5—C6—C1	−178.8 (5)	C9—C8—C14—C13	1.9 (8)
N2—N1—C7—C5	−173.7 (4)	S1—C8—C14—C13	178.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82 (2)	1.91 (5)	2.589 (6)	139 (7)
N2—H2A···O1i	0.86 (2)	2.05 (2)	2.914 (6)	173 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82 (2)	1.91 (5)	2.589 (6)	139 (7)
N2—H2A⋯O1i	0.86 (2)	2.05 (2)	2.914 (6)	173 (6)

Symmetry code: (i) .