organic compounds
N′-[(E)-2-Hydroxy-5-iodobenzylidene]-4-methylbenzenesulfonohydrazide
aDepartment of Chemistry, Faculty of Science, University of Zanjan, 45371-38791 Zanjan, Iran, and bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
*Correspondence e-mail: m_ghorbanloo@yahoo.com
In the title molecule, C14H13IN2O3S, the dihedral angle between the planes of the benzene and toluene rings is 84.3 (3)°. The molecule displays a trans conformation with respect to the C=N bond. There is an intramolecular O—H⋯N hydrogen bond with the azomethine N atom as acceptor. In the crystal, N—H⋯O hydrogen bonds connect the molecules into chains running along the b axis.
Related literature
For background to 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 in sulfonohydrazides, see: Kia et al. (2008); Tai et al. (2009).
see: KayserExperimental
Crystal data
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Data collection: X-AREA (Stoe & Cie, 2005); cell 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).
Supporting information
10.1107/S1600536812035738/bt5993sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812035738/bt5993Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812035738/bt5993Isup3.cml
For preparing the title compound, a methanol (10 ml) solution of 2-hydroxy-5-iodobenzaldehyde (2 mmol) was dropwise added to a methanol solution (10 ml) of 4-methyl-benzenesulfonic acid hydrazide (2 mmol), and the mixture was refluxed for 3 hrs. Then the solution was evaporated on a steam bath to 5 ml and cooled to room temperature. A white precipitate of the title compound was separated and filtered off, washed with 5 ml of cooled methanol and then dried in air. X-ray quality crystals of the title compound were obtained from methanol by slow solvent evaporation. Yield: 90%. Selected IR (cm-1): 3464 (w, broad), 3140 (m), 1619 (s), 1481 (vs), 1359 (s), 1329 (vs), 1264 (vs), 1177 (s), 1087 (s), 956 (vs), 869 (vs) 772 (s), 666 (s), 545 (s), 458 (m).
The hydrogen atoms bonded to O and N atoms were found in difference Fourier map and there coordinates were refined with Uiso(H) = 1.2 Ueq(O,N). The O—H and N—H distances were restrained to 0.82 (2)Å and 0.86 (2)Å, respectively. H atoms bonded to C were positioned geometrically and refined as riding atoms with C—H = 0.96 Å and Uiso(H) = 1.5 Ueq(C) for the methyl group and C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C) for the other H atoms.
Data collection: X-AREA (Stoe & Cie, 2005); cell
X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); 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).The molecular structure of the title compound with atom labels. Anisotropic displacement ellipsoids drawn at 30% probability level for non-H atoms. The packing diagram of the title compound. Hydrogen bonds are shown as blue dashed line. |
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 | Absolute structure parameter: −0.06 (3) |
C14H13IN2O3S | V = 776.6 (3) Å3 |
Mr = 416.23 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.2467 (12) Å | µ = 2.21 mm−1 |
b = 10.394 (2) Å | T = 298 K |
c = 11.971 (2) Å | 0.50 × 0.40 × 0.20 mm |
β = 92.42 (3)° |
Stoe IPDS 2 diffractometer | 3841 independent reflections |
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005) | 2791 reflections with I > 2σ(I) |
Tmin = 0.405, Tmax = 0.667 | Rint = 0.059 |
6035 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.114 | Δρmax = 0.88 e Å−3 |
S = 0.92 | Δρmin = −0.99 e Å−3 |
3841 reflections | Absolute structure: Flack (1983), 1641 Friedel pairs |
197 parameters | Absolute structure parameter: −0.06 (3) |
3 restraints |
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) |
Symmetry code: (i) −x, y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C14H13IN2O3S |
Mr | 416.23 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 6.2467 (12), 10.394 (2), 11.971 (2) |
β (°) | 92.42 (3) |
V (Å3) | 776.6 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.21 |
Crystal size (mm) | 0.50 × 0.40 × 0.20 |
Data collection | |
Diffractometer | Stoe IPDS 2 diffractometer |
Absorption correction | Numerical (X-SHAPE; Stoe & Cie, 2005) |
Tmin, Tmax | 0.405, 0.667 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6035, 3841, 2791 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.687 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.114, 0.92 |
No. of reflections | 3841 |
No. of parameters | 197 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.88, −0.99 |
Absolute structure | Flack (1983), 1641 Friedel pairs |
Absolute structure parameter | −0.06 (3) |
Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
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) −x, y+1/2, −z. |
Acknowledgements
The authors are grateful to the University of Zanjan for financial support.
References
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Sulfonyl hydrazones are found to exhibit large medicinal applications. Similar to sulfonamides, sulfonyl hydrazones also have various biological activities (Kayser et al., 2004). For example, imidosulfonylhydrazones have antibacterial and antineociceptive properties (Silva et al., 2006). Acidic sulfonyl hydrazone derivatives have analgesic and anti-inflammatory activities. On the other hand, polymorphism is a phenomenon wherein the same substances exhibits different crystal packing arrangements and is of practical importance e.g., pharmaceutical processes where different physical properties of polymorphic forms can substantially alter the viability and quality of product. Plymorphism is another interesting subject in sulfonyl hydrazones. sulfonyl hydrazones derived from the condensation of O-hydroxy aldehydes and sulfonyl acid hydrazides can form different polymorphs. Kia et al. (2008) and Tai et al. (2009) have reported two polymorph of these type of compounds.
We report here the crystal structure of (E)-N'-(2-hydroxy-5-iodobenzylidene)-4-methylbenzenesulfonohydrazide. The asymmetric unit of the title compound contains one molecule, which is shown in Fig. 1. Bond distances and bond angles are in the normal range of similar compounds (Shahverdizadeh et al., 2011; Ali et al., 2007; Tierney et al., 2006). The molecule displays trans configuration with respect to the C=N bond. The packing diagram of the title compound is shown in Fig. 2. In the title compound, the dihedral angle between the planes of benzene and toluene rings is 84.3 (3)°. There is an intramolecular O—H···N hydrogen bond in which the nitrogen of the azomethine group (–C=N–) acting as hydrogen bond acceptor. Intermolecular N—H···O hydrogen bond stabilize the crystal structure (Fig. 2 & Table 1).