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Acta Cryst. (2008). E64, o921    [ doi:10.1107/S1600536808011136 ]

N'-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene)benzenesulfonohydrazide

H. M. Ali, M. Laila, M. R. Rizal and S. W. Ng

Abstract top

The molecule of the title compound, C14H10FN3O3S, consists of an indole unit and a phenylsulfonyl unit that are disposed in an approximately trans orientation relative to the N-N single bond. Two molecules are arranged about a center of inversion, forming a hydrazide-carbonyl N-H...O hydrogen-bonded dimer; the dimers are linked by an indole-sulfonyl N-H...O hydrogen bond into a ribbon.

Comment top

We have reported the crystal structures of 3-indole benzenesulfonohydrazides (Ali et al., 2007a, 2007b, 2007c). The studies continue with the benzenesulfonohydrazide that is obtained by condensing benzenesulfonohydrazine with a substituted 1H-indol-2,3-dione, 5-fluroisatin. This compound exists as a hydrogen-bonded dimer (Naumov et al., 2000). The title compound (Scheme I) has the indolyl fused-ring portion and the phenylsulfonyl portion disposed in an approximately trans-alignment relative to the N–N single-bond (Fig. 1). Two molecules are arranged about a center-of-inversion to form an N–Hhydrazide···Ocarbonyl hydrogen-bonded dimer; the dimers are linked by another N–Hindole···Osulfonyl hydrogen bond into a ribbon structure (Fig. 2).

Related literature top

For the crystal structures of related 3-indole benzenesulfonylhydrazones, see: Ali et al. (2007a,b,c). For the crystal structure of 5-fluro-1H-indole-2,3-dione, see: Naumov et al. (2000).

Experimental top

Benzenesulfonyl hydrazide (0. 69 g, 4 mmol) and 5-fluoroisatin (0.66 g, 4 mmol) were heated in ethanol (50 ml) for an hour. The solution when cooled afforded yellow crystals.

Refinement top

The carbon-bound H atoms were placed at calculated positions (C–H 0.95 Å), and were included in the refinement in the riding model approximation with U(H) set to 1.2Ueq(C). The amino H atoms were located in a difference Fouier map, and were refined with a distance restraint of N–H 0.88±0.01 Å.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of C14H10FN3O3S. Displacement ellipsoids are drawn at the 70% probability level, and H atoms are shown as spheres of arbitrary radii.
[Figure 2] Fig. 2. Ribbon structure of C10H10FN3O3S.
N'-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene)benzenesulfonohydrazide top
Crystal data top
C14H10FN3O3SF000 = 656
Mr = 319.31Dx = 1.535 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6063 reflections
a = 8.2218 (2) Åθ = 3.0–31.3º
b = 16.4933 (3) ŵ = 0.26 mm−1
c = 10.8585 (2) ÅT = 123 (2) K
β = 110.249 (1)ºIrregular block, yellow
V = 1381.46 (5) Å30.50 × 0.20 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		3166 independent reflections
Radiation source: medium-focus sealed tube2741 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.024
T = 123(2) Kθmax = 27.5º
φ and ω scansθmin = 2.4º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −10→10
Tmin = 0.816, Tmax = 0.962k = −21→21
10513 measured reflectionsl = −13→14
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.145  w = 1/[σ2(Fo2) + (0.0922P)2 + 0.2432P]
where P = (Fo2 + 2Fc2)/3
S = 1.20(Δ/σ)max = 0.001
3166 reflectionsΔρmax = 0.54 e Å−3
207 parametersΔρmin = −0.59 e Å−3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C14H10FN3O3SV = 1381.46 (5) Å3
Mr = 319.31Z = 4
Monoclinic, P21/cMo Kα
a = 8.2218 (2) ŵ = 0.26 mm−1
b = 16.4933 (3) ÅT = 123 (2) K
c = 10.8585 (2) Å0.50 × 0.20 × 0.15 mm
β = 110.249 (1)º
Data collection top
Bruker SMART APEX
diffractometer		3166 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2741 reflections with I > 2σ(I)
Tmin = 0.816, Tmax = 0.962Rint = 0.024
10513 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0362 restraints
wR(F2) = 0.145H atoms treated by a mixture of
independent and constrained refinement
S = 1.20Δρmax = 0.54 e Å−3
3166 reflectionsΔρmin = −0.59 e Å−3
207 parameters
Special details top

Experimental. A medium-focus collimator of 0.8 mm diameter was used on the diffractometer to measure the somewhat large crystal.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.65386 (5)0.28692 (2)0.54366 (4)0.01609 (16)
O10.61921 (18)0.21966 (7)0.61409 (14)0.0248 (3)
O20.56524 (17)0.29375 (8)0.40497 (13)0.0255 (3)
O30.42474 (17)0.51614 (8)0.60498 (13)0.0240 (3)
N10.59808 (19)0.37034 (9)0.60384 (14)0.0183 (3)
H1N0.557 (3)0.4089 (11)0.546 (2)0.036 (7)*
N20.67998 (18)0.38149 (8)0.73560 (14)0.0172 (3)
N30.5337 (2)0.57008 (9)0.81558 (16)0.0232 (3)
H3N0.478 (3)0.6168 (9)0.799 (2)0.038 (7)*
C10.8794 (2)0.29132 (9)0.58025 (17)0.0165 (3)
C20.9467 (3)0.33843 (13)0.50285 (19)0.0277 (4)
H20.87300.36960.43180.033*
C31.1256 (3)0.33841 (16)0.5329 (2)0.0368 (5)
H31.17540.37030.48230.044*
C41.2315 (3)0.29211 (13)0.6361 (2)0.0349 (5)
H41.35300.29140.65410.042*
C51.1624 (2)0.24721 (12)0.7127 (2)0.0300 (4)
H51.23640.21640.78410.036*
C60.9846 (2)0.24692 (10)0.68578 (19)0.0227 (4)
H60.93600.21670.73900.027*
C70.6472 (2)0.44753 (10)0.78623 (17)0.0174 (3)
C80.7275 (2)0.47125 (10)0.92317 (17)0.0182 (4)
C90.8561 (2)0.43576 (10)1.02774 (17)0.0219 (4)
H90.90690.38531.01920.026*
C100.9065 (3)0.47769 (11)1.14518 (18)0.0252 (4)
C110.8372 (3)0.55171 (11)1.16168 (19)0.0285 (4)
H110.87650.57791.24470.034*
C120.7090 (3)0.58763 (11)1.05538 (19)0.0276 (4)
H120.65970.63851.06410.033*
C130.6564 (2)0.54660 (10)0.93715 (18)0.0204 (4)
C140.5206 (2)0.51454 (10)0.72023 (17)0.0187 (4)
F11.03509 (17)0.44573 (7)1.25055 (11)0.0374 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0133 (2)0.0151 (2)0.0192 (3)−0.00149 (13)0.00483 (17)−0.00402 (14)
O10.0232 (7)0.0164 (6)0.0388 (8)−0.0042 (5)0.0157 (6)−0.0018 (5)
O20.0199 (7)0.0309 (7)0.0207 (7)−0.0001 (5)0.0006 (5)−0.0086 (5)
O30.0257 (7)0.0238 (6)0.0195 (6)0.0050 (5)0.0039 (5)−0.0003 (5)
N10.0202 (7)0.0158 (7)0.0180 (7)0.0032 (5)0.0053 (6)−0.0009 (5)
N20.0179 (7)0.0163 (7)0.0179 (7)−0.0007 (5)0.0069 (6)−0.0010 (5)
N30.0250 (8)0.0194 (7)0.0219 (8)0.0074 (6)0.0039 (6)−0.0024 (6)
C10.0132 (8)0.0191 (8)0.0172 (8)−0.0017 (6)0.0053 (6)−0.0053 (6)
C20.0251 (9)0.0409 (11)0.0185 (9)−0.0057 (8)0.0093 (7)0.0000 (8)
C30.0284 (10)0.0596 (14)0.0287 (11)−0.0140 (10)0.0178 (9)−0.0058 (10)
C40.0153 (9)0.0477 (13)0.0424 (12)−0.0030 (8)0.0108 (9)−0.0180 (10)
C50.0196 (9)0.0262 (10)0.0370 (11)0.0035 (7)0.0005 (8)−0.0062 (8)
C60.0202 (8)0.0180 (8)0.0269 (9)0.0000 (6)0.0042 (7)0.0001 (7)
C70.0182 (8)0.0154 (7)0.0191 (8)0.0007 (6)0.0072 (7)0.0000 (6)
C80.0223 (8)0.0144 (7)0.0183 (8)−0.0007 (6)0.0076 (7)−0.0013 (6)
C90.0266 (9)0.0166 (8)0.0207 (9)0.0012 (6)0.0059 (7)0.0019 (6)
C100.0287 (9)0.0225 (9)0.0197 (9)−0.0010 (7)0.0023 (7)0.0037 (7)
C110.0364 (11)0.0251 (9)0.0202 (9)−0.0022 (8)0.0052 (8)−0.0058 (7)
C120.0327 (10)0.0217 (9)0.0251 (10)0.0039 (8)0.0059 (8)−0.0073 (7)
C130.0216 (8)0.0180 (8)0.0206 (9)0.0019 (6)0.0060 (7)−0.0008 (6)
C140.0184 (8)0.0172 (8)0.0206 (9)0.0016 (6)0.0069 (7)0.0005 (6)
F10.0471 (8)0.0298 (6)0.0211 (6)0.0055 (5)−0.0061 (5)0.0026 (5)
Geometric parameters (Å, °) top
S1—O11.4309 (13)C4—C51.375 (3)
S1—O21.4325 (14)C4—H40.9500
S1—N11.6545 (14)C5—C61.388 (3)
S1—C11.7582 (17)C5—H50.9500
O3—C141.227 (2)C6—H60.9500
N1—N21.367 (2)C7—C81.456 (2)
N1—H1N0.876 (10)C7—C141.518 (2)
N2—C71.290 (2)C8—C91.385 (2)
N3—C141.358 (2)C8—C131.404 (2)
N3—C131.410 (2)C9—C101.382 (3)
N3—H3N0.884 (10)C9—H90.9500
C1—C61.383 (2)C10—F11.366 (2)
C1—C21.392 (3)C10—C111.385 (3)
C2—C31.392 (3)C11—C121.397 (3)
C2—H20.9500C11—H110.9500
C3—C41.386 (3)C12—C131.382 (3)
C3—H30.9500C12—H120.9500
O1—S1—O2119.99 (8)C1—C6—C5118.97 (18)
O1—S1—N1107.46 (8)C1—C6—H6120.5
O2—S1—N1103.90 (8)C5—C6—H6120.5
O1—S1—C1107.50 (8)N2—C7—C8125.06 (15)
O2—S1—C1110.32 (8)N2—C7—C14128.61 (16)
N1—S1—C1106.93 (7)C8—C7—C14106.32 (14)
N2—N1—S1114.96 (11)C9—C8—C13120.91 (16)
N2—N1—H1N125.5 (17)C9—C8—C7132.16 (16)
S1—N1—H1N114.2 (17)C13—C8—C7106.84 (15)
C7—N2—N1117.39 (14)C10—C9—C8116.43 (16)
C14—N3—C13111.76 (15)C10—C9—H9121.8
C14—N3—H3N122.4 (17)C8—C9—H9121.8
C13—N3—H3N125.6 (17)F1—C10—C9118.54 (17)
C6—C1—C2122.02 (17)F1—C10—C11117.74 (17)
C6—C1—S1118.29 (14)C9—C10—C11123.70 (17)
C2—C1—S1119.69 (14)C10—C11—C12119.57 (17)
C1—C2—C3117.85 (19)C10—C11—H11120.2
C1—C2—H2121.1C12—C11—H11120.2
C3—C2—H2121.1C13—C12—C11117.64 (17)
C4—C3—C2120.4 (2)C13—C12—H12121.2
C4—C3—H3119.8C11—C12—H12121.2
C2—C3—H3119.8C12—C13—C8121.74 (17)
C5—C4—C3120.72 (19)C12—C13—N3128.89 (16)
C5—C4—H4119.6C8—C13—N3109.37 (15)
C3—C4—H4119.6O3—C14—N3128.06 (16)
C4—C5—C6119.97 (19)O3—C14—C7126.22 (15)
C4—C5—H5120.0N3—C14—C7105.70 (15)
C6—C5—H5120.0
O1—S1—N1—N257.51 (14)C14—C7—C8—C13−0.74 (19)
O2—S1—N1—N2−174.35 (12)C13—C8—C9—C101.2 (3)
C1—S1—N1—N2−57.66 (14)C7—C8—C9—C10177.29 (18)
S1—N1—N2—C7176.78 (12)C8—C9—C10—F1−178.89 (16)
O1—S1—C1—C6−14.56 (16)C8—C9—C10—C11−0.6 (3)
O2—S1—C1—C6−147.07 (13)F1—C10—C11—C12178.16 (18)
N1—S1—C1—C6100.57 (14)C9—C10—C11—C12−0.1 (3)
O1—S1—C1—C2165.08 (14)C10—C11—C12—C130.3 (3)
O2—S1—C1—C232.58 (16)C11—C12—C13—C80.3 (3)
N1—S1—C1—C2−79.78 (16)C11—C12—C13—N3−178.45 (19)
C6—C1—C2—C31.4 (3)C9—C8—C13—C12−1.1 (3)
S1—C1—C2—C3−178.20 (16)C7—C8—C13—C12−178.09 (17)
C1—C2—C3—C40.5 (3)C9—C8—C13—N3177.87 (16)
C2—C3—C4—C5−1.8 (3)C7—C8—C13—N30.9 (2)
C3—C4—C5—C61.0 (3)C14—N3—C13—C12178.14 (19)
C2—C1—C6—C5−2.2 (3)C14—N3—C13—C8−0.8 (2)
S1—C1—C6—C5177.47 (14)C13—N3—C14—O3178.88 (18)
C4—C5—C6—C10.9 (3)C13—N3—C14—C70.3 (2)
N1—N2—C7—C8−177.31 (15)N2—C7—C14—O30.9 (3)
N1—N2—C7—C143.5 (3)C8—C7—C14—O3−178.35 (17)
N2—C7—C8—C93.5 (3)N2—C7—C14—N3179.59 (17)
C14—C7—C8—C9−177.21 (18)C8—C7—C14—N30.29 (19)
N2—C7—C8—C13179.93 (17)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O3i0.88 (1)2.10 (2)2.896 (2)151 (2)
N3—H3n···O1ii0.88 (1)2.22 (2)2.986 (2)145 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y+1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O3i0.88 (1)2.10 (2)2.896 (2)151 (2)
N3—H3n···O1ii0.88 (1)2.22 (2)2.986 (2)145 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y+1/2, −z+3/2.
Acknowledgements top

The authors thank the University of Canterbury, New Zealand, for the diffraction measurements, and the Science Fund (12–02–03–2031) for supporting this study.

references
References top

Ali, H. M., Nazzatush Shimar, J., Wan Jefrey, B. & Ng, S. W. (2007a). Acta Cryst. E63, o1807–o1808.

Ali, H. M., Yusnita, J., Wan Jefrey, B. & Ng, S. W. (2007b). Acta Cryst. E63, o1621–o1622.

Ali, H. M., Yusnita, J., Wan Jefrey, B. & Ng, S. W. (2007c). Acta Cryst. E63, o3513–?.

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Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Naumov, P., Anastasova, F., Drew, M. G. B. & Ng, S. W. (2000). Acta Cryst. C56, e406–e407.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2008). publCIF. In preparation.