N'-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl-idene)benzene-sulfono-hydrazide.

The mol-ecule of the title compound, C(14)H(10)FN(3)O(3)S, 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 mol-ecules 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 crystal structure of 5-fluoro-1H-indole-2,3-dione, see: Naumov et al. (2000 ▶).

Experimental

Crystal data

C14H10FN3O3S

M = 319.31

Monoclinic,

a = 8.2218 (2) Å

b = 16.4933 (3) Å

c = 10.8585 (2) Å

β = 110.249 (1)°

V = 1381.46 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 123 (2) K

0.50 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.816, T max = 0.962

10513 measured reflections

3166 independent reflections

2741 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.145

S = 1.20

3166 reflections

207 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011136/sg2224sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011136/sg2224Isup2.hkl

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

C14H10FN3O3S	F000 = 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 = 3.0–31.3º
b = 16.4933 (3) Å	µ = 0.26 mm−1
c = 10.8585 (2) Å	T = 123 (2) K
β = 110.249 (1)º	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)
Monochromator: graphite	Rint = 0.024
T = 123(2) K	θmax = 27.5º
φ and ω scans	θmin = 2.4º
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	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H 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 reflections	Δρmax = 0.54 e Å−3
207 parameters	Δρmin = −0.59 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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)

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) .