organic compounds
N′-[1-(2-Hydroxyphenyl)ethylidene]benzenesulfonohydrazide
aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and bWeifang Institute of Supervision and Inspection of product Quality, Weifang 261061, People's Republic of China
*Correspondence e-mail: taixishi@lzu.edu.cn
In the title compound, C14H14N2O3S, the conformation is stabilized by an intramoleclar O—H⋯N hydrogen bond and the dihedral angle between the aromatic ring planes is 79.55 (18)°. In the intermolecular N—H⋯O hydrogen bonds lead to [100] chains of molecules.
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808010970/hb2723sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010970/hb2723Isup2.hkl
3 mmol of 2'-hydroxyacetophenone (3 mmol) was added to a solution of benzenesulfonyl hydrazide (3 mmol) in 10 ml of 95% ethanol. The mixture was continuously stirred for 3 h at refluxing temperature, evaporating some ethanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 68%). Colourless blocks of (I) were obtained by evaporation from a methanol solution after 3 days.
The H atoms were placed geometrically (C—H = 0.93–0.96 Å, O—H = 0.82Å, N—H = 0.90 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of (I) showing 40% displacement ellipsoids (arbitrary spheres for the H atoms). The hydrogen bond is indicated by a double-dashed line. |
C14H14N2O3S | F(000) = 608 |
Mr = 290.33 | Dx = 1.362 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2187 reflections |
a = 5.2435 (9) Å | θ = 2.5–26.2° |
b = 13.2515 (18) Å | µ = 0.24 mm−1 |
c = 20.375 (2) Å | T = 298 K |
β = 90.531 (2)° | Block, colourless |
V = 1415.7 (3) Å3 | 0.50 × 0.40 × 0.37 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 2484 independent reflections |
Radiation source: fine-focus sealed tube | 1755 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −6→6 |
Tmin = 0.891, Tmax = 0.918 | k = −15→15 |
7165 measured reflections | l = −20→24 |
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)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.0428P)2 + 0.8643P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2484 reflections | Δρmax = 0.26 e Å−3 |
182 parameters | Δρmin = −0.26 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: 0.018 (2) |
C14H14N2O3S | V = 1415.7 (3) Å3 |
Mr = 290.33 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.2435 (9) Å | µ = 0.24 mm−1 |
b = 13.2515 (18) Å | T = 298 K |
c = 20.375 (2) Å | 0.50 × 0.40 × 0.37 mm |
β = 90.531 (2)° |
Bruker SMART CCD diffractometer | 2484 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1755 reflections with I > 2σ(I) |
Tmin = 0.891, Tmax = 0.918 | Rint = 0.062 |
7165 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.26 e Å−3 |
2484 reflections | Δρmin = −0.26 e Å−3 |
182 parameters |
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 | ||
N1 | 0.3921 (4) | 0.13317 (15) | 0.94596 (10) | 0.0397 (6) | |
H1 | 0.5569 | 0.1345 | 0.9587 | 0.048* | |
N2 | 0.3516 (4) | 0.21056 (16) | 0.90070 (10) | 0.0378 (5) | |
O1 | 0.2888 (4) | 0.06000 (14) | 1.05125 (9) | 0.0589 (6) | |
O2 | −0.0427 (4) | 0.15363 (16) | 0.98874 (10) | 0.0560 (6) | |
O3 | 0.0643 (4) | 0.35673 (15) | 0.86405 (10) | 0.0590 (6) | |
H3 | 0.1123 | 0.3112 | 0.8884 | 0.089* | |
S1 | 0.21361 (14) | 0.14329 (5) | 1.01133 (3) | 0.0403 (3) | |
C1 | 0.2935 (5) | 0.2560 (2) | 1.05229 (13) | 0.0414 (7) | |
C2 | 0.1465 (7) | 0.3404 (2) | 1.04223 (18) | 0.0659 (10) | |
H2 | 0.0090 | 0.3388 | 1.0131 | 0.079* | |
C3 | 0.2063 (10) | 0.4282 (3) | 1.0763 (2) | 0.0931 (14) | |
H3A | 0.1108 | 0.4864 | 1.0694 | 0.112* | |
C4 | 0.4057 (10) | 0.4288 (4) | 1.1200 (3) | 0.1013 (16) | |
H4 | 0.4428 | 0.4871 | 1.1436 | 0.122* | |
C5 | 0.5504 (8) | 0.3446 (4) | 1.1293 (2) | 0.0922 (14) | |
H5 | 0.6876 | 0.3463 | 1.1586 | 0.111* | |
C6 | 0.4952 (6) | 0.2567 (3) | 1.09574 (17) | 0.0651 (9) | |
H6 | 0.5928 | 0.1990 | 1.1024 | 0.078* | |
C7 | 0.6988 (6) | 0.1407 (2) | 0.83455 (14) | 0.0472 (7) | |
H7A | 0.8593 | 0.1693 | 0.8479 | 0.071* | |
H7B | 0.7018 | 0.1265 | 0.7884 | 0.071* | |
H7C | 0.6699 | 0.0793 | 0.8584 | 0.071* | |
C8 | 0.4892 (5) | 0.21397 (19) | 0.84856 (12) | 0.0357 (6) | |
C9 | 0.4232 (5) | 0.29502 (19) | 0.80152 (12) | 0.0381 (6) | |
C10 | 0.2176 (5) | 0.3608 (2) | 0.81077 (13) | 0.0421 (7) | |
C11 | 0.1611 (6) | 0.4351 (2) | 0.76493 (15) | 0.0553 (8) | |
H11 | 0.0230 | 0.4779 | 0.7716 | 0.066* | |
C12 | 0.3072 (7) | 0.4462 (3) | 0.70987 (16) | 0.0619 (9) | |
H12 | 0.2675 | 0.4960 | 0.6793 | 0.074* | |
C13 | 0.5109 (7) | 0.3840 (3) | 0.70007 (15) | 0.0631 (9) | |
H13 | 0.6118 | 0.3920 | 0.6631 | 0.076* | |
C14 | 0.5665 (6) | 0.3096 (2) | 0.74492 (14) | 0.0524 (8) | |
H14 | 0.7047 | 0.2673 | 0.7373 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0424 (14) | 0.0379 (12) | 0.0388 (12) | 0.0084 (10) | 0.0018 (10) | 0.0056 (10) |
N2 | 0.0423 (13) | 0.0336 (12) | 0.0374 (12) | 0.0046 (10) | −0.0001 (10) | 0.0029 (10) |
O1 | 0.0933 (17) | 0.0375 (11) | 0.0461 (12) | 0.0088 (11) | 0.0154 (11) | 0.0074 (9) |
O2 | 0.0413 (13) | 0.0634 (14) | 0.0636 (13) | −0.0068 (10) | 0.0049 (10) | −0.0136 (11) |
O3 | 0.0633 (15) | 0.0536 (13) | 0.0605 (13) | 0.0217 (11) | 0.0148 (11) | 0.0146 (10) |
S1 | 0.0473 (5) | 0.0335 (4) | 0.0402 (4) | 0.0002 (3) | 0.0065 (3) | −0.0006 (3) |
C1 | 0.0423 (17) | 0.0383 (15) | 0.0436 (16) | −0.0023 (12) | 0.0051 (13) | −0.0047 (12) |
C2 | 0.081 (3) | 0.0445 (19) | 0.073 (2) | 0.0108 (17) | −0.0073 (19) | −0.0115 (16) |
C3 | 0.123 (4) | 0.046 (2) | 0.111 (3) | 0.009 (2) | 0.011 (3) | −0.022 (2) |
C4 | 0.102 (4) | 0.084 (3) | 0.118 (4) | −0.034 (3) | 0.012 (3) | −0.050 (3) |
C5 | 0.069 (3) | 0.114 (4) | 0.094 (3) | −0.019 (3) | −0.012 (2) | −0.045 (3) |
C6 | 0.048 (2) | 0.074 (2) | 0.073 (2) | 0.0026 (17) | −0.0069 (18) | −0.0137 (18) |
C7 | 0.0505 (19) | 0.0457 (16) | 0.0457 (16) | 0.0071 (14) | 0.0069 (14) | −0.0027 (13) |
C8 | 0.0362 (15) | 0.0342 (14) | 0.0366 (14) | −0.0051 (12) | −0.0013 (12) | −0.0055 (11) |
C9 | 0.0418 (17) | 0.0361 (14) | 0.0363 (14) | −0.0049 (12) | −0.0048 (12) | −0.0004 (11) |
C10 | 0.0421 (17) | 0.0400 (15) | 0.0442 (16) | −0.0037 (13) | −0.0021 (13) | 0.0025 (13) |
C11 | 0.056 (2) | 0.0466 (18) | 0.063 (2) | 0.0022 (15) | −0.0082 (16) | 0.0154 (15) |
C12 | 0.071 (2) | 0.059 (2) | 0.055 (2) | −0.0072 (18) | −0.0139 (18) | 0.0214 (16) |
C13 | 0.076 (3) | 0.069 (2) | 0.0450 (18) | −0.0073 (19) | 0.0049 (17) | 0.0140 (16) |
C14 | 0.056 (2) | 0.0562 (19) | 0.0448 (17) | 0.0011 (15) | 0.0025 (15) | 0.0065 (14) |
N1—N2 | 1.394 (3) | C5—H5 | 0.9300 |
N1—S1 | 1.641 (2) | C6—H6 | 0.9300 |
N1—H1 | 0.9000 | C7—C8 | 1.496 (4) |
N2—C8 | 1.291 (3) | C7—H7A | 0.9600 |
O1—S1 | 1.4246 (19) | C7—H7B | 0.9600 |
O2—S1 | 1.423 (2) | C7—H7C | 0.9600 |
O3—C10 | 1.358 (3) | C8—C9 | 1.478 (4) |
O3—H3 | 0.8200 | C9—C14 | 1.395 (4) |
S1—C1 | 1.760 (3) | C9—C10 | 1.401 (4) |
C1—C2 | 1.372 (4) | C10—C11 | 1.387 (4) |
C1—C6 | 1.373 (4) | C11—C12 | 1.372 (4) |
C2—C3 | 1.390 (5) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C12—C13 | 1.366 (5) |
C3—C4 | 1.367 (6) | C12—H12 | 0.9300 |
C3—H3A | 0.9300 | C13—C14 | 1.374 (4) |
C4—C5 | 1.361 (6) | C13—H13 | 0.9300 |
C4—H4 | 0.9300 | C14—H14 | 0.9300 |
C5—C6 | 1.380 (5) | ||
N2—N1—S1 | 113.09 (16) | C5—C6—H6 | 120.6 |
N2—N1—H1 | 108.5 | C8—C7—H7A | 109.5 |
S1—N1—H1 | 108.5 | C8—C7—H7B | 109.5 |
C8—N2—N1 | 119.2 (2) | H7A—C7—H7B | 109.5 |
C10—O3—H3 | 109.5 | C8—C7—H7C | 109.5 |
O2—S1—O1 | 120.99 (14) | H7A—C7—H7C | 109.5 |
O2—S1—N1 | 106.82 (12) | H7B—C7—H7C | 109.5 |
O1—S1—N1 | 104.08 (11) | N2—C8—C9 | 115.5 (2) |
O2—S1—C1 | 106.95 (13) | N2—C8—C7 | 123.5 (2) |
O1—S1—C1 | 108.88 (13) | C9—C8—C7 | 121.0 (2) |
N1—S1—C1 | 108.63 (12) | C14—C9—C10 | 116.5 (2) |
C2—C1—C6 | 121.3 (3) | C14—C9—C8 | 120.8 (2) |
C2—C1—S1 | 119.3 (2) | C10—C9—C8 | 122.7 (2) |
C6—C1—S1 | 119.3 (2) | O3—C10—C11 | 116.3 (3) |
C1—C2—C3 | 118.9 (4) | O3—C10—C9 | 123.0 (2) |
C1—C2—H2 | 120.5 | C11—C10—C9 | 120.7 (3) |
C3—C2—H2 | 120.5 | C12—C11—C10 | 120.6 (3) |
C4—C3—C2 | 119.9 (4) | C12—C11—H11 | 119.7 |
C4—C3—H3A | 120.1 | C10—C11—H11 | 119.7 |
C2—C3—H3A | 120.1 | C13—C12—C11 | 119.9 (3) |
C5—C4—C3 | 120.5 (4) | C13—C12—H12 | 120.1 |
C5—C4—H4 | 119.7 | C11—C12—H12 | 120.1 |
C3—C4—H4 | 119.7 | C12—C13—C14 | 119.8 (3) |
C4—C5—C6 | 120.6 (4) | C12—C13—H13 | 120.1 |
C4—C5—H5 | 119.7 | C14—C13—H13 | 120.1 |
C6—C5—H5 | 119.7 | C13—C14—C9 | 122.4 (3) |
C1—C6—C5 | 118.8 (4) | C13—C14—H14 | 118.8 |
C1—C6—H6 | 120.6 | C9—C14—H14 | 118.8 |
S1—N1—N2—C8 | 176.68 (19) | N1—N2—C8—C9 | 176.6 (2) |
N2—N1—S1—O2 | 52.5 (2) | N1—N2—C8—C7 | −2.1 (4) |
N2—N1—S1—O1 | −178.43 (18) | N2—C8—C9—C14 | 176.8 (2) |
N2—N1—S1—C1 | −62.5 (2) | C7—C8—C9—C14 | −4.5 (4) |
O2—S1—C1—C2 | −17.1 (3) | N2—C8—C9—C10 | −3.1 (4) |
O1—S1—C1—C2 | −149.4 (3) | C7—C8—C9—C10 | 175.6 (3) |
N1—S1—C1—C2 | 97.9 (3) | C14—C9—C10—O3 | −178.9 (3) |
O2—S1—C1—C6 | 160.2 (2) | C8—C9—C10—O3 | 1.0 (4) |
O1—S1—C1—C6 | 27.9 (3) | C14—C9—C10—C11 | 0.8 (4) |
N1—S1—C1—C6 | −84.8 (3) | C8—C9—C10—C11 | −179.3 (3) |
C6—C1—C2—C3 | 0.8 (5) | O3—C10—C11—C12 | 179.1 (3) |
S1—C1—C2—C3 | 178.0 (3) | C9—C10—C11—C12 | −0.6 (5) |
C1—C2—C3—C4 | −1.3 (6) | C10—C11—C12—C13 | −0.3 (5) |
C2—C3—C4—C5 | 1.6 (7) | C11—C12—C13—C14 | 1.0 (5) |
C3—C4—C5—C6 | −1.3 (7) | C12—C13—C14—C9 | −0.7 (5) |
C2—C1—C6—C5 | −0.5 (5) | C10—C9—C14—C13 | −0.2 (4) |
S1—C1—C6—C5 | −177.7 (3) | C8—C9—C14—C13 | 180.0 (3) |
C4—C5—C6—C1 | 0.7 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N2 | 0.82 | 1.85 | 2.561 (3) | 145 |
N1—H1···O2i | 0.90 | 2.20 | 3.093 (3) | 174 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C14H14N2O3S |
Mr | 290.33 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 5.2435 (9), 13.2515 (18), 20.375 (2) |
β (°) | 90.531 (2) |
V (Å3) | 1415.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.50 × 0.40 × 0.37 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.891, 0.918 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7165, 2484, 1755 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.131, 1.04 |
No. of reflections | 2484 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.26 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N2 | 0.82 | 1.85 | 2.561 (3) | 145 |
N1—H1···O2i | 0.90 | 2.20 | 3.093 (3) | 174 |
Symmetry code: (i) x+1, y, z. |
Acknowledgements
The authors thank the National Natural Science Foundation of China (20671073), the Natural Science Foundation of Shandong (Y2007B60), and the Science and Technology Foundation of Weifang University for research grants.
References
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tai, X.-S., Yin, X.-H., Tan, M.-Y. & Li, Y.-Z. (2003). Acta Cryst. E59, o681–o682. Web of Science CSD CrossRef IUCr Journals Google Scholar
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As part of our ongoing studies of the coordination chemistry of aroylhydrazones as potential ligands (Tai et al., 2003), we now report the synthesis and structure of the title compound, (I), (Fig. 1).
The molecular conformation is stabilised by an intramoleclar O-H···N hydrogen bond (Table 1) and the dihedral angle between the aromatic ring planes is 79.55 (18)°. In the crystal, an intermolecular N-H···O hydrogen bond lead to [100] chains of molecules.