PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o904.
Published online 2008 April 26. doi:  10.1107/S1600536808010970
PMCID: PMC2961334

N′-[1-(2-Hydroxy­phen­yl)ethyl­idene]benzene­sulfonohydrazide

Abstract

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 crystal structure, inter­molecular N—H(...)O hydrogen bonds lead to [100] chains of mol­ecules.

Related literature

For related literature, see: Tai et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o904-scheme1.jpg

Experimental

Crystal data

  • C14H14N2O3S
  • M r = 290.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o904-efi1.jpg
  • a = 5.2435 (9) Å
  • b = 13.2515 (18) Å
  • c = 20.375 (2) Å
  • β = 90.531 (2)°
  • V = 1415.7 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 298 (2) K
  • 0.50 × 0.40 × 0.37 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.891, T max = 0.918
  • 7165 measured reflections
  • 2484 independent reflections
  • 1755 reflections with I > 2σ(I)
  • R int = 0.062

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.131
  • S = 1.04
  • 2484 reflections
  • 182 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010970/hb2723sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010970/hb2723Isup2.hkl

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

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

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).

Figures

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.

Crystal data

C14H14N2O3SF000 = 608
Mr = 290.33Dx = 1.362 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2187 reflections
a = 5.2435 (9) Åθ = 2.5–26.2º
b = 13.2515 (18) ŵ = 0.24 mm1
c = 20.375 (2) ÅT = 298 (2) K
β = 90.531 (2)ºBlock, colourless
V = 1415.7 (3) Å30.50 × 0.40 × 0.37 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer2484 independent reflections
Radiation source: fine-focus sealed tube1755 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.062
T = 298(2) Kθmax = 25.0º
ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2000)h = −6→6
Tmin = 0.891, Tmax = 0.918k = −15→15
7165 measured reflectionsl = −20→24

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047  w = 1/[σ2(Fo2) + (0.0428P)2 + 0.8643P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.131(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.26 e Å3
2484 reflectionsΔρmin = −0.26 e Å3
182 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.018 (2)
Secondary atom site location: difference Fourier map

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.3921 (4)0.13317 (15)0.94596 (10)0.0397 (6)
H10.55690.13450.95870.048*
N20.3516 (4)0.21056 (16)0.90070 (10)0.0378 (5)
O10.2888 (4)0.06000 (14)1.05125 (9)0.0589 (6)
O2−0.0427 (4)0.15363 (16)0.98874 (10)0.0560 (6)
O30.0643 (4)0.35673 (15)0.86405 (10)0.0590 (6)
H30.11230.31120.88840.089*
S10.21361 (14)0.14329 (5)1.01133 (3)0.0403 (3)
C10.2935 (5)0.2560 (2)1.05229 (13)0.0414 (7)
C20.1465 (7)0.3404 (2)1.04223 (18)0.0659 (10)
H20.00900.33881.01310.079*
C30.2063 (10)0.4282 (3)1.0763 (2)0.0931 (14)
H3A0.11080.48641.06940.112*
C40.4057 (10)0.4288 (4)1.1200 (3)0.1013 (16)
H40.44280.48711.14360.122*
C50.5504 (8)0.3446 (4)1.1293 (2)0.0922 (14)
H50.68760.34631.15860.111*
C60.4952 (6)0.2567 (3)1.09574 (17)0.0651 (9)
H60.59280.19901.10240.078*
C70.6988 (6)0.1407 (2)0.83455 (14)0.0472 (7)
H7A0.85930.16930.84790.071*
H7B0.70180.12650.78840.071*
H7C0.66990.07930.85840.071*
C80.4892 (5)0.21397 (19)0.84856 (12)0.0357 (6)
C90.4232 (5)0.29502 (19)0.80152 (12)0.0381 (6)
C100.2176 (5)0.3608 (2)0.81077 (13)0.0421 (7)
C110.1611 (6)0.4351 (2)0.76493 (15)0.0553 (8)
H110.02300.47790.77160.066*
C120.3072 (7)0.4462 (3)0.70987 (16)0.0619 (9)
H120.26750.49600.67930.074*
C130.5109 (7)0.3840 (3)0.70007 (15)0.0631 (9)
H130.61180.39200.66310.076*
C140.5665 (6)0.3096 (2)0.74492 (14)0.0524 (8)
H140.70470.26730.73730.063*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0424 (14)0.0379 (12)0.0388 (12)0.0084 (10)0.0018 (10)0.0056 (10)
N20.0423 (13)0.0336 (12)0.0374 (12)0.0046 (10)−0.0001 (10)0.0029 (10)
O10.0933 (17)0.0375 (11)0.0461 (12)0.0088 (11)0.0154 (11)0.0074 (9)
O20.0413 (13)0.0634 (14)0.0636 (13)−0.0068 (10)0.0049 (10)−0.0136 (11)
O30.0633 (15)0.0536 (13)0.0605 (13)0.0217 (11)0.0148 (11)0.0146 (10)
S10.0473 (5)0.0335 (4)0.0402 (4)0.0002 (3)0.0065 (3)−0.0006 (3)
C10.0423 (17)0.0383 (15)0.0436 (16)−0.0023 (12)0.0051 (13)−0.0047 (12)
C20.081 (3)0.0445 (19)0.073 (2)0.0108 (17)−0.0073 (19)−0.0115 (16)
C30.123 (4)0.046 (2)0.111 (3)0.009 (2)0.011 (3)−0.022 (2)
C40.102 (4)0.084 (3)0.118 (4)−0.034 (3)0.012 (3)−0.050 (3)
C50.069 (3)0.114 (4)0.094 (3)−0.019 (3)−0.012 (2)−0.045 (3)
C60.048 (2)0.074 (2)0.073 (2)0.0026 (17)−0.0069 (18)−0.0137 (18)
C70.0505 (19)0.0457 (16)0.0457 (16)0.0071 (14)0.0069 (14)−0.0027 (13)
C80.0362 (15)0.0342 (14)0.0366 (14)−0.0051 (12)−0.0013 (12)−0.0055 (11)
C90.0418 (17)0.0361 (14)0.0363 (14)−0.0049 (12)−0.0048 (12)−0.0004 (11)
C100.0421 (17)0.0400 (15)0.0442 (16)−0.0037 (13)−0.0021 (13)0.0025 (13)
C110.056 (2)0.0466 (18)0.063 (2)0.0022 (15)−0.0082 (16)0.0154 (15)
C120.071 (2)0.059 (2)0.055 (2)−0.0072 (18)−0.0139 (18)0.0214 (16)
C130.076 (3)0.069 (2)0.0450 (18)−0.0073 (19)0.0049 (17)0.0140 (16)
C140.056 (2)0.0562 (19)0.0448 (17)0.0011 (15)0.0025 (15)0.0065 (14)

Geometric parameters (Å, °)

N1—N21.394 (3)C5—H50.9300
N1—S11.641 (2)C6—H60.9300
N1—H10.9000C7—C81.496 (4)
N2—C81.291 (3)C7—H7A0.9600
O1—S11.4246 (19)C7—H7B0.9600
O2—S11.423 (2)C7—H7C0.9600
O3—C101.358 (3)C8—C91.478 (4)
O3—H30.8200C9—C141.395 (4)
S1—C11.760 (3)C9—C101.401 (4)
C1—C21.372 (4)C10—C111.387 (4)
C1—C61.373 (4)C11—C121.372 (4)
C2—C31.390 (5)C11—H110.9300
C2—H20.9300C12—C131.366 (5)
C3—C41.367 (6)C12—H120.9300
C3—H3A0.9300C13—C141.374 (4)
C4—C51.361 (6)C13—H130.9300
C4—H40.9300C14—H140.9300
C5—C61.380 (5)
N2—N1—S1113.09 (16)C5—C6—H6120.6
N2—N1—H1108.5C8—C7—H7A109.5
S1—N1—H1108.5C8—C7—H7B109.5
C8—N2—N1119.2 (2)H7A—C7—H7B109.5
C10—O3—H3109.5C8—C7—H7C109.5
O2—S1—O1120.99 (14)H7A—C7—H7C109.5
O2—S1—N1106.82 (12)H7B—C7—H7C109.5
O1—S1—N1104.08 (11)N2—C8—C9115.5 (2)
O2—S1—C1106.95 (13)N2—C8—C7123.5 (2)
O1—S1—C1108.88 (13)C9—C8—C7121.0 (2)
N1—S1—C1108.63 (12)C14—C9—C10116.5 (2)
C2—C1—C6121.3 (3)C14—C9—C8120.8 (2)
C2—C1—S1119.3 (2)C10—C9—C8122.7 (2)
C6—C1—S1119.3 (2)O3—C10—C11116.3 (3)
C1—C2—C3118.9 (4)O3—C10—C9123.0 (2)
C1—C2—H2120.5C11—C10—C9120.7 (3)
C3—C2—H2120.5C12—C11—C10120.6 (3)
C4—C3—C2119.9 (4)C12—C11—H11119.7
C4—C3—H3A120.1C10—C11—H11119.7
C2—C3—H3A120.1C13—C12—C11119.9 (3)
C5—C4—C3120.5 (4)C13—C12—H12120.1
C5—C4—H4119.7C11—C12—H12120.1
C3—C4—H4119.7C12—C13—C14119.8 (3)
C4—C5—C6120.6 (4)C12—C13—H13120.1
C4—C5—H5119.7C14—C13—H13120.1
C6—C5—H5119.7C13—C14—C9122.4 (3)
C1—C6—C5118.8 (4)C13—C14—H14118.8
C1—C6—H6120.6C9—C14—H14118.8
S1—N1—N2—C8176.68 (19)N1—N2—C8—C9176.6 (2)
N2—N1—S1—O252.5 (2)N1—N2—C8—C7−2.1 (4)
N2—N1—S1—O1−178.43 (18)N2—C8—C9—C14176.8 (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—C10175.6 (3)
N1—S1—C1—C297.9 (3)C14—C9—C10—O3−178.9 (3)
O2—S1—C1—C6160.2 (2)C8—C9—C10—O31.0 (4)
O1—S1—C1—C627.9 (3)C14—C9—C10—C110.8 (4)
N1—S1—C1—C6−84.8 (3)C8—C9—C10—C11−179.3 (3)
C6—C1—C2—C30.8 (5)O3—C10—C11—C12179.1 (3)
S1—C1—C2—C3178.0 (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—C51.6 (7)C11—C12—C13—C141.0 (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—C13180.0 (3)
C4—C5—C6—C10.7 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···N20.821.852.561 (3)145
N1—H1···O2i0.902.203.093 (3)174

Symmetry codes: (i) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2723).

References

  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tai, X.-S., Yin, X.-H., Tan, M.-Y. & Li, Y.-Z. (2003). Acta Cryst. E59, o681–o682.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography