organic compounds
N′-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene)benzenesulfonohydrazide
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
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.
Related literature
For the crystal structures of related 3-indole benzenesulfonylhydrazones, see: Ali et al. (2007a,b,c). For the of 5-fluoro-1H-indole-2,3-dione, see: Naumov et al. (2000).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; 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).
Supporting information
10.1107/S1600536808011136/sg2224sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808011136/sg2224Isup2.hkl
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.
The carbon-bound H atoms were placed at calculated positions (C–H 0.95 Å), and were included in the
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.Data collection: APEX2 (Bruker, 2005); cell
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).C14H10FN3O3S | F(000) = 656 |
Mr = 319.31 | Dx = 1.535 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6063 reflections |
a = 8.2218 (2) Å | θ = 3.0–31.3° |
b = 16.4933 (3) Å | µ = 0.26 mm−1 |
c = 10.8585 (2) Å | T = 123 K |
β = 110.249 (1)° | Irregular block, yellow |
V = 1381.46 (5) Å3 | 0.50 × 0.20 × 0.15 mm |
Z = 4 |
Bruker SMART APEX diffractometer | 3166 independent reflections |
Radiation source: medium-focus sealed tube | 2741 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ϕ and ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.816, Tmax = 0.962 | k = −21→21 |
10513 measured reflections | l = −13→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.20 | w = 1/[σ2(Fo2) + (0.0922P)2 + 0.2432P] where P = (Fo2 + 2Fc2)/3 |
3166 reflections | (Δ/σ)max = 0.001 |
207 parameters | Δρmax = 0.54 e Å−3 |
2 restraints | Δρmin = −0.60 e Å−3 |
C14H10FN3O3S | V = 1381.46 (5) Å3 |
Mr = 319.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.2218 (2) Å | µ = 0.26 mm−1 |
b = 16.4933 (3) Å | T = 123 K |
c = 10.8585 (2) Å | 0.50 × 0.20 × 0.15 mm |
β = 110.249 (1)° |
Bruker SMART APEX diffractometer | 3166 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2741 reflections with I > 2σ(I) |
Tmin = 0.816, Tmax = 0.962 | Rint = 0.024 |
10513 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 2 restraints |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.20 | Δρmax = 0.54 e Å−3 |
3166 reflections | Δρmin = −0.60 e Å−3 |
207 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.65386 (5) | 0.28692 (2) | 0.54366 (4) | 0.01609 (16) | |
O1 | 0.61921 (18) | 0.21966 (7) | 0.61409 (14) | 0.0248 (3) | |
O2 | 0.56524 (17) | 0.29375 (8) | 0.40497 (13) | 0.0255 (3) | |
O3 | 0.42474 (17) | 0.51614 (8) | 0.60498 (13) | 0.0240 (3) | |
N1 | 0.59808 (19) | 0.37034 (9) | 0.60384 (14) | 0.0183 (3) | |
H1N | 0.557 (3) | 0.4089 (11) | 0.546 (2) | 0.036 (7)* | |
N2 | 0.67998 (18) | 0.38149 (8) | 0.73560 (14) | 0.0172 (3) | |
N3 | 0.5337 (2) | 0.57008 (9) | 0.81558 (16) | 0.0232 (3) | |
H3N | 0.478 (3) | 0.6168 (9) | 0.799 (2) | 0.038 (7)* | |
C1 | 0.8794 (2) | 0.29132 (9) | 0.58025 (17) | 0.0165 (3) | |
C2 | 0.9467 (3) | 0.33843 (13) | 0.50285 (19) | 0.0277 (4) | |
H2 | 0.8730 | 0.3696 | 0.4318 | 0.033* | |
C3 | 1.1256 (3) | 0.33841 (16) | 0.5329 (2) | 0.0368 (5) | |
H3 | 1.1754 | 0.3703 | 0.4823 | 0.044* | |
C4 | 1.2315 (3) | 0.29211 (13) | 0.6361 (2) | 0.0349 (5) | |
H4 | 1.3530 | 0.2914 | 0.6541 | 0.042* | |
C5 | 1.1624 (2) | 0.24721 (12) | 0.7127 (2) | 0.0300 (4) | |
H5 | 1.2364 | 0.2164 | 0.7841 | 0.036* | |
C6 | 0.9846 (2) | 0.24692 (10) | 0.68578 (19) | 0.0227 (4) | |
H6 | 0.9360 | 0.2167 | 0.7390 | 0.027* | |
C7 | 0.6472 (2) | 0.44753 (10) | 0.78623 (17) | 0.0174 (3) | |
C8 | 0.7275 (2) | 0.47125 (10) | 0.92317 (17) | 0.0182 (4) | |
C9 | 0.8561 (2) | 0.43576 (10) | 1.02774 (17) | 0.0219 (4) | |
H9 | 0.9069 | 0.3853 | 1.0192 | 0.026* | |
C10 | 0.9065 (3) | 0.47769 (11) | 1.14518 (18) | 0.0252 (4) | |
C11 | 0.8372 (3) | 0.55171 (11) | 1.16168 (19) | 0.0285 (4) | |
H11 | 0.8765 | 0.5779 | 1.2447 | 0.034* | |
C12 | 0.7090 (3) | 0.58763 (11) | 1.05538 (19) | 0.0276 (4) | |
H12 | 0.6597 | 0.6385 | 1.0641 | 0.033* | |
C13 | 0.6564 (2) | 0.54660 (10) | 0.93715 (18) | 0.0204 (4) | |
C14 | 0.5206 (2) | 0.51454 (10) | 0.72023 (17) | 0.0187 (4) | |
F1 | 1.03509 (17) | 0.44573 (7) | 1.25055 (11) | 0.0374 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0133 (2) | 0.0151 (2) | 0.0192 (3) | −0.00149 (13) | 0.00483 (17) | −0.00402 (14) |
O1 | 0.0232 (7) | 0.0164 (6) | 0.0388 (8) | −0.0042 (5) | 0.0157 (6) | −0.0018 (5) |
O2 | 0.0199 (7) | 0.0309 (7) | 0.0207 (7) | −0.0001 (5) | 0.0006 (5) | −0.0086 (5) |
O3 | 0.0257 (7) | 0.0238 (6) | 0.0195 (6) | 0.0050 (5) | 0.0039 (5) | −0.0003 (5) |
N1 | 0.0202 (7) | 0.0158 (7) | 0.0180 (7) | 0.0032 (5) | 0.0053 (6) | −0.0009 (5) |
N2 | 0.0179 (7) | 0.0163 (7) | 0.0179 (7) | −0.0007 (5) | 0.0069 (6) | −0.0010 (5) |
N3 | 0.0250 (8) | 0.0194 (7) | 0.0219 (8) | 0.0074 (6) | 0.0039 (6) | −0.0024 (6) |
C1 | 0.0132 (8) | 0.0191 (8) | 0.0172 (8) | −0.0017 (6) | 0.0053 (6) | −0.0053 (6) |
C2 | 0.0251 (9) | 0.0409 (11) | 0.0185 (9) | −0.0057 (8) | 0.0093 (7) | 0.0000 (8) |
C3 | 0.0284 (10) | 0.0596 (14) | 0.0287 (11) | −0.0140 (10) | 0.0178 (9) | −0.0058 (10) |
C4 | 0.0153 (9) | 0.0477 (13) | 0.0424 (12) | −0.0030 (8) | 0.0108 (9) | −0.0180 (10) |
C5 | 0.0196 (9) | 0.0262 (10) | 0.0370 (11) | 0.0035 (7) | 0.0005 (8) | −0.0062 (8) |
C6 | 0.0202 (8) | 0.0180 (8) | 0.0269 (9) | 0.0000 (6) | 0.0042 (7) | 0.0001 (7) |
C7 | 0.0182 (8) | 0.0154 (7) | 0.0191 (8) | 0.0007 (6) | 0.0072 (7) | 0.0000 (6) |
C8 | 0.0223 (8) | 0.0144 (7) | 0.0183 (8) | −0.0007 (6) | 0.0076 (7) | −0.0013 (6) |
C9 | 0.0266 (9) | 0.0166 (8) | 0.0207 (9) | 0.0012 (6) | 0.0059 (7) | 0.0019 (6) |
C10 | 0.0287 (9) | 0.0225 (9) | 0.0197 (9) | −0.0010 (7) | 0.0023 (7) | 0.0037 (7) |
C11 | 0.0364 (11) | 0.0251 (9) | 0.0202 (9) | −0.0022 (8) | 0.0052 (8) | −0.0058 (7) |
C12 | 0.0327 (10) | 0.0217 (9) | 0.0251 (10) | 0.0039 (8) | 0.0059 (8) | −0.0073 (7) |
C13 | 0.0216 (8) | 0.0180 (8) | 0.0206 (9) | 0.0019 (6) | 0.0060 (7) | −0.0008 (6) |
C14 | 0.0184 (8) | 0.0172 (8) | 0.0206 (9) | 0.0016 (6) | 0.0069 (7) | 0.0005 (6) |
F1 | 0.0471 (8) | 0.0298 (6) | 0.0211 (6) | 0.0055 (5) | −0.0061 (5) | 0.0026 (5) |
S1—O1 | 1.4309 (13) | C4—C5 | 1.375 (3) |
S1—O2 | 1.4325 (14) | C4—H4 | 0.9500 |
S1—N1 | 1.6545 (14) | C5—C6 | 1.388 (3) |
S1—C1 | 1.7582 (17) | C5—H5 | 0.9500 |
O3—C14 | 1.227 (2) | C6—H6 | 0.9500 |
N1—N2 | 1.367 (2) | C7—C8 | 1.456 (2) |
N1—H1N | 0.876 (10) | C7—C14 | 1.518 (2) |
N2—C7 | 1.290 (2) | C8—C9 | 1.385 (2) |
N3—C14 | 1.358 (2) | C8—C13 | 1.404 (2) |
N3—C13 | 1.410 (2) | C9—C10 | 1.382 (3) |
N3—H3N | 0.884 (10) | C9—H9 | 0.9500 |
C1—C6 | 1.383 (2) | C10—F1 | 1.366 (2) |
C1—C2 | 1.392 (3) | C10—C11 | 1.385 (3) |
C2—C3 | 1.392 (3) | C11—C12 | 1.397 (3) |
C2—H2 | 0.9500 | C11—H11 | 0.9500 |
C3—C4 | 1.386 (3) | C12—C13 | 1.382 (3) |
C3—H3 | 0.9500 | C12—H12 | 0.9500 |
O1—S1—O2 | 119.99 (8) | C1—C6—C5 | 118.97 (18) |
O1—S1—N1 | 107.46 (8) | C1—C6—H6 | 120.5 |
O2—S1—N1 | 103.90 (8) | C5—C6—H6 | 120.5 |
O1—S1—C1 | 107.50 (8) | N2—C7—C8 | 125.06 (15) |
O2—S1—C1 | 110.32 (8) | N2—C7—C14 | 128.61 (16) |
N1—S1—C1 | 106.93 (7) | C8—C7—C14 | 106.32 (14) |
N2—N1—S1 | 114.96 (11) | C9—C8—C13 | 120.91 (16) |
N2—N1—H1N | 125.5 (17) | C9—C8—C7 | 132.16 (16) |
S1—N1—H1N | 114.2 (17) | C13—C8—C7 | 106.84 (15) |
C7—N2—N1 | 117.39 (14) | C10—C9—C8 | 116.43 (16) |
C14—N3—C13 | 111.76 (15) | C10—C9—H9 | 121.8 |
C14—N3—H3N | 122.4 (17) | C8—C9—H9 | 121.8 |
C13—N3—H3N | 125.6 (17) | F1—C10—C9 | 118.54 (17) |
C6—C1—C2 | 122.02 (17) | F1—C10—C11 | 117.74 (17) |
C6—C1—S1 | 118.29 (14) | C9—C10—C11 | 123.70 (17) |
C2—C1—S1 | 119.69 (14) | C10—C11—C12 | 119.57 (17) |
C1—C2—C3 | 117.85 (19) | C10—C11—H11 | 120.2 |
C1—C2—H2 | 121.1 | C12—C11—H11 | 120.2 |
C3—C2—H2 | 121.1 | C13—C12—C11 | 117.64 (17) |
C4—C3—C2 | 120.4 (2) | C13—C12—H12 | 121.2 |
C4—C3—H3 | 119.8 | C11—C12—H12 | 121.2 |
C2—C3—H3 | 119.8 | C12—C13—C8 | 121.74 (17) |
C5—C4—C3 | 120.72 (19) | C12—C13—N3 | 128.89 (16) |
C5—C4—H4 | 119.6 | C8—C13—N3 | 109.37 (15) |
C3—C4—H4 | 119.6 | O3—C14—N3 | 128.06 (16) |
C4—C5—C6 | 119.97 (19) | O3—C14—C7 | 126.22 (15) |
C4—C5—H5 | 120.0 | N3—C14—C7 | 105.70 (15) |
C6—C5—H5 | 120.0 | ||
O1—S1—N1—N2 | 57.51 (14) | C14—C7—C8—C13 | −0.74 (19) |
O2—S1—N1—N2 | −174.35 (12) | C13—C8—C9—C10 | 1.2 (3) |
C1—S1—N1—N2 | −57.66 (14) | C7—C8—C9—C10 | 177.29 (18) |
S1—N1—N2—C7 | 176.78 (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—C12 | 178.16 (18) |
N1—S1—C1—C6 | 100.57 (14) | C9—C10—C11—C12 | −0.1 (3) |
O1—S1—C1—C2 | 165.08 (14) | C10—C11—C12—C13 | 0.3 (3) |
O2—S1—C1—C2 | 32.58 (16) | C11—C12—C13—C8 | 0.3 (3) |
N1—S1—C1—C2 | −79.78 (16) | C11—C12—C13—N3 | −178.45 (19) |
C6—C1—C2—C3 | 1.4 (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—C4 | 0.5 (3) | C9—C8—C13—N3 | 177.87 (16) |
C2—C3—C4—C5 | −1.8 (3) | C7—C8—C13—N3 | 0.9 (2) |
C3—C4—C5—C6 | 1.0 (3) | C14—N3—C13—C12 | 178.14 (19) |
C2—C1—C6—C5 | −2.2 (3) | C14—N3—C13—C8 | −0.8 (2) |
S1—C1—C6—C5 | 177.47 (14) | C13—N3—C14—O3 | 178.88 (18) |
C4—C5—C6—C1 | 0.9 (3) | C13—N3—C14—C7 | 0.3 (2) |
N1—N2—C7—C8 | −177.31 (15) | N2—C7—C14—O3 | 0.9 (3) |
N1—N2—C7—C14 | 3.5 (3) | C8—C7—C14—O3 | −178.35 (17) |
N2—C7—C8—C9 | 3.5 (3) | N2—C7—C14—N3 | 179.59 (17) |
C14—C7—C8—C9 | −177.21 (18) | C8—C7—C14—N3 | 0.29 (19) |
N2—C7—C8—C13 | 179.93 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n···O3i | 0.88 (1) | 2.10 (2) | 2.896 (2) | 151 (2) |
N3—H3n···O1ii | 0.88 (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. |
Experimental details
Crystal data | |
Chemical formula | C14H10FN3O3S |
Mr | 319.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 123 |
a, b, c (Å) | 8.2218 (2), 16.4933 (3), 10.8585 (2) |
β (°) | 110.249 (1) |
V (Å3) | 1381.46 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.50 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.816, 0.962 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10513, 3166, 2741 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.145, 1.20 |
No. of reflections | 3166 |
No. of parameters | 207 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.54, −0.60 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n···O3i | 0.88 (1) | 2.10 (2) | 2.896 (2) | 151 (2) |
N3—H3n···O1ii | 0.88 (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
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
Ali, H. M., Nazzatush Shimar, J., Wan Jefrey, B. & Ng, S. W. (2007a). Acta Cryst. E63, o1807–o1808. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ali, H. M., Yusnita, J., Wan Jefrey, B. & Ng, S. W. (2007b). Acta Cryst. E63, o1621–o1622. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ali, H. M., Yusnita, J., Wan Jefrey, B. & Ng, S. W. (2007c). Acta Cryst. E63, o3513. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Naumov, P., Anastasova, F., Drew, M. G. B. & Ng, S. W. (2000). Acta Cryst. C56, e406–e407. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar
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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).