(Z)-4-(3-Fluoro-phen-yl)-1-(5-nitro-2-oxo-indolin-3-yl-idene)thio-semicarbazide.

In the title compound, C(15)H(10)FN(5)O(3)S, an intra-molecular N-H⋯N hydrogen bond generates an S(5) ring, whereas N-H⋯O and C-H⋯S inter-actions complete S(6) ring motifs. The dihedral angle between the isatin ring system and the fluoro-benzene ring is 5.96 (6)° and the complete mol-ecule is close to planar (r.m.s. deviation for all the non-H atoms = 0.112 Å). In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds to form C(8) chains along the [100] direction and C-H⋯O inter-actions are also observed.

Related literature

For background to isatin derivatives, see: Pervez et al. (2010 ▶); Pervez, Ramzan et al. (2011 ▶); Pervez, Saira et al. (2011 ▶). For related structures, see: Pervez et al. (2009 ▶); Ramzan et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H10FN5O3S

M = 359.34

Orthorhombic,

a = 18.2485 (5) Å

b = 8.8043 (2) Å

c = 18.6913 (5) Å

V = 3003.04 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.957, T max = 0.966

53231 measured reflections

3728 independent reflections

3101 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.06

3728 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005053/hb6630sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005053/hb6630Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005053/hb6630Isup3.cml

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

C15H10FN5O3S	F(000) = 1472
Mr = 359.34	Dx = 1.590 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3101 reflections
a = 18.2485 (5) Å	θ = 2.2–28.3°
b = 8.8043 (2) Å	µ = 0.26 mm−1
c = 18.6913 (5) Å	T = 296 K
V = 3003.04 (13) Å3	Prism, orange
Z = 8	0.30 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	3728 independent reflections
Radiation source: fine-focus sealed tube	3101 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 7.50 pixels mm-1	θmax = 28.3°, θmin = 2.2°
ω scans	h = −24→21
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→11
Tmin = 0.957, Tmax = 0.966	l = −24→24
53231 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.045P)2 + 1.1466P] where P = (Fo2 + 2Fc2)/3
3728 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S1	0.23197 (2)	0.67952 (5)	−0.04002 (2)	0.0468 (1)
F1	0.41277 (8)	1.02225 (17)	−0.14952 (9)	0.1015 (6)
O1	0.14958 (6)	0.37037 (13)	0.13575 (6)	0.0491 (4)
O2	0.50290 (8)	0.02530 (18)	0.34644 (8)	0.0759 (5)
O3	0.53143 (7)	0.1873 (2)	0.26498 (9)	0.0811 (6)
N1	0.36565 (7)	0.62197 (15)	0.01839 (7)	0.0421 (4)
N2	0.26518 (6)	0.51166 (14)	0.06902 (6)	0.0388 (3)
N3	0.31021 (6)	0.43761 (13)	0.11392 (6)	0.0361 (3)
N4	0.19541 (6)	0.21196 (13)	0.22400 (7)	0.0379 (3)
N5	0.48641 (8)	0.11444 (18)	0.29912 (8)	0.0531 (4)
C1	0.41226 (8)	0.72152 (17)	−0.01991 (8)	0.0400 (4)
C2	0.38746 (9)	0.8269 (2)	−0.06921 (10)	0.0535 (5)
C3	0.43845 (11)	0.9188 (2)	−0.10154 (11)	0.0600 (6)
C4	0.51147 (11)	0.9129 (2)	−0.08870 (11)	0.0608 (6)
C5	0.53538 (10)	0.8073 (2)	−0.03948 (10)	0.0599 (6)
C6	0.48660 (9)	0.7113 (2)	−0.00505 (9)	0.0493 (5)
C7	0.29264 (8)	0.60528 (15)	0.01605 (7)	0.0363 (4)
C8	0.28008 (7)	0.34713 (15)	0.15985 (7)	0.0329 (3)
C9	0.20008 (7)	0.31556 (15)	0.16965 (8)	0.0358 (4)
C10	0.26468 (7)	0.17306 (15)	0.24998 (7)	0.0336 (3)
C11	0.31818 (7)	0.25505 (15)	0.21213 (7)	0.0324 (3)
C12	0.39169 (7)	0.23766 (16)	0.22778 (7)	0.0365 (4)
C13	0.40880 (8)	0.13552 (17)	0.28157 (8)	0.0402 (4)
C14	0.35672 (9)	0.05368 (18)	0.31899 (8)	0.0445 (5)
C15	0.28301 (8)	0.07168 (17)	0.30351 (8)	0.0412 (4)
H1	0.38771	0.56263	0.04792	0.0505*
H2	0.33789	0.83526	−0.08008	0.0643*
H2A	0.21856	0.50064	0.07329	0.0466*
H4	0.54402	0.97735	−0.11205	0.0730*
H4A	0.15495	0.17542	0.24013	0.0455*
H5	0.58513	0.80035	−0.02920	0.0719*
H6	0.50361	0.64038	0.02787	0.0592*
H12	0.42774	0.29165	0.20349	0.0438*
H14	0.37122	−0.01361	0.35464	0.0534*
H15	0.24724	0.01765	0.32818	0.0494*

	U11	U22	U33	U12	U13	U23
S1	0.0420 (2)	0.0503 (2)	0.0480 (2)	−0.0007 (2)	−0.0056 (2)	0.0107 (2)
F1	0.0892 (9)	0.0919 (9)	0.1234 (12)	0.0074 (8)	0.0314 (9)	0.0678 (9)
O1	0.0316 (5)	0.0552 (7)	0.0604 (7)	0.0046 (5)	−0.0063 (5)	0.0088 (5)
O2	0.0683 (9)	0.0887 (10)	0.0707 (9)	0.0296 (8)	−0.0231 (7)	0.0079 (8)
O3	0.0348 (6)	0.1214 (14)	0.0871 (10)	0.0002 (7)	−0.0130 (7)	0.0148 (10)
N1	0.0375 (6)	0.0419 (7)	0.0469 (7)	0.0005 (5)	0.0005 (5)	0.0107 (5)
N2	0.0337 (6)	0.0396 (6)	0.0432 (6)	−0.0012 (5)	−0.0009 (5)	0.0070 (5)
N3	0.0362 (6)	0.0333 (6)	0.0389 (6)	0.0002 (5)	−0.0010 (5)	0.0017 (5)
N4	0.0283 (5)	0.0390 (6)	0.0464 (6)	−0.0019 (5)	0.0049 (5)	0.0012 (5)
N5	0.0425 (7)	0.0670 (9)	0.0498 (7)	0.0149 (7)	−0.0125 (6)	−0.0093 (7)
C1	0.0388 (7)	0.0389 (7)	0.0424 (7)	−0.0022 (6)	0.0064 (6)	−0.0028 (6)
C2	0.0431 (8)	0.0528 (10)	0.0647 (10)	0.0002 (7)	0.0091 (8)	0.0175 (8)
C3	0.0615 (11)	0.0509 (10)	0.0677 (11)	−0.0007 (8)	0.0196 (9)	0.0155 (8)
C4	0.0591 (10)	0.0562 (10)	0.0672 (11)	−0.0165 (9)	0.0247 (9)	−0.0065 (9)
C5	0.0416 (9)	0.0712 (12)	0.0670 (11)	−0.0132 (8)	0.0075 (8)	−0.0133 (10)
C6	0.0422 (8)	0.0554 (10)	0.0504 (8)	−0.0035 (7)	−0.0001 (7)	−0.0041 (7)
C7	0.0403 (7)	0.0310 (6)	0.0376 (7)	−0.0005 (5)	0.0017 (5)	−0.0013 (5)
C8	0.0294 (6)	0.0326 (6)	0.0368 (6)	0.0004 (5)	−0.0009 (5)	−0.0013 (5)
C9	0.0299 (6)	0.0342 (7)	0.0432 (7)	0.0005 (5)	0.0003 (5)	−0.0024 (6)
C10	0.0320 (6)	0.0326 (6)	0.0362 (6)	0.0011 (5)	0.0026 (5)	−0.0045 (5)
C11	0.0309 (6)	0.0316 (6)	0.0347 (6)	0.0008 (5)	0.0007 (5)	−0.0020 (5)
C12	0.0308 (6)	0.0401 (7)	0.0387 (7)	−0.0002 (5)	−0.0007 (5)	−0.0031 (6)
C13	0.0365 (7)	0.0454 (8)	0.0388 (7)	0.0080 (6)	−0.0069 (6)	−0.0068 (6)
C14	0.0532 (9)	0.0428 (8)	0.0375 (7)	0.0086 (7)	−0.0030 (6)	0.0023 (6)
C15	0.0457 (8)	0.0391 (7)	0.0389 (7)	0.0001 (6)	0.0053 (6)	0.0023 (6)

S1—C7	1.6587 (14)	C3—C4	1.355 (3)
F1—C3	1.361 (2)	C4—C5	1.379 (3)
O1—C9	1.2180 (17)	C5—C6	1.386 (2)
O2—N5	1.220 (2)	C8—C9	1.4974 (18)
O3—N5	1.222 (2)	C8—C11	1.4476 (18)
N1—C1	1.416 (2)	C10—C15	1.382 (2)
N1—C7	1.3411 (19)	C10—C11	1.4053 (18)
N2—N3	1.3434 (16)	C11—C12	1.3815 (18)
N2—C7	1.3823 (18)	C12—C13	1.385 (2)
N3—C8	1.2938 (17)	C13—C14	1.383 (2)
N4—C9	1.3679 (19)	C14—C15	1.385 (2)
N4—C10	1.3968 (17)	C2—H2	0.9300
N5—C13	1.466 (2)	C4—H4	0.9300
N1—H1	0.8600	C5—H5	0.9300
N2—H2A	0.8600	C6—H6	0.9300
N4—H4A	0.8600	C12—H12	0.9300
C1—C6	1.388 (2)	C14—H14	0.9300
C1—C2	1.384 (2)	C15—H15	0.9300
C2—C3	1.373 (3)
C1—N1—C7	130.41 (13)	O1—C9—C8	126.90 (13)
N3—N2—C7	121.01 (11)	N4—C9—C8	105.98 (11)
N2—N3—C8	116.96 (11)	O1—C9—N4	127.11 (12)
C9—N4—C10	111.43 (11)	C11—C10—C15	121.88 (12)
O2—N5—O3	123.39 (16)	N4—C10—C11	109.13 (11)
O2—N5—C13	118.82 (14)	N4—C10—C15	128.99 (12)
O3—N5—C13	117.79 (14)	C8—C11—C12	132.17 (12)
C1—N1—H1	115.00	C8—C11—C10	107.09 (11)
C7—N1—H1	115.00	C10—C11—C12	120.74 (12)
N3—N2—H2A	119.00	C11—C12—C13	116.41 (12)
C7—N2—H2A	119.00	N5—C13—C12	117.56 (13)
C9—N4—H4A	124.00	N5—C13—C14	119.02 (14)
C10—N4—H4A	124.00	C12—C13—C14	123.42 (14)
N1—C1—C2	123.74 (14)	C13—C14—C15	120.15 (14)
N1—C1—C6	116.49 (14)	C10—C15—C14	117.40 (13)
C2—C1—C6	119.77 (14)	C1—C2—H2	121.00
C1—C2—C3	117.81 (16)	C3—C2—H2	121.00
F1—C3—C4	118.74 (17)	C3—C4—H4	121.00
C2—C3—C4	124.46 (18)	C5—C4—H4	121.00
F1—C3—C2	116.80 (17)	C4—C5—H5	119.00
C3—C4—C5	117.08 (18)	C6—C5—H5	119.00
C4—C5—C6	121.18 (17)	C1—C6—H6	120.00
C1—C6—C5	119.70 (16)	C5—C6—H6	120.00
S1—C7—N2	116.46 (11)	C11—C12—H12	122.00
S1—C7—N1	129.83 (11)	C13—C12—H12	122.00
N1—C7—N2	113.71 (12)	C13—C14—H14	120.00
C9—C8—C11	106.36 (11)	C15—C14—H14	120.00
N3—C8—C9	127.58 (12)	C10—C15—H15	121.00
N3—C8—C11	126.06 (12)	C14—C15—H15	121.00
C7—N1—C1—C2	0.8 (3)	C2—C3—C4—C5	−0.3 (3)
C7—N1—C1—C6	179.82 (15)	C3—C4—C5—C6	0.3 (3)
C1—N1—C7—S1	8.9 (2)	C4—C5—C6—C1	−0.3 (3)
C1—N1—C7—N2	−170.96 (14)	N3—C8—C9—O1	−0.1 (2)
C7—N2—N3—C8	−177.01 (12)	N3—C8—C9—N4	179.51 (13)
N3—N2—C7—S1	175.28 (10)	C11—C8—C9—O1	−179.74 (14)
N3—N2—C7—N1	−4.80 (18)	C11—C8—C9—N4	−0.17 (15)
N2—N3—C8—C9	−0.6 (2)	N3—C8—C11—C10	−179.13 (13)
N2—N3—C8—C11	179.00 (12)	N3—C8—C11—C12	0.3 (2)
C10—N4—C9—O1	179.28 (14)	C9—C8—C11—C10	0.57 (14)
C10—N4—C9—C8	−0.30 (15)	C9—C8—C11—C12	179.97 (16)
C9—N4—C10—C11	0.67 (16)	N4—C10—C11—C8	−0.76 (15)
C9—N4—C10—C15	−179.04 (14)	N4—C10—C11—C12	179.74 (12)
O2—N5—C13—C12	179.84 (15)	C15—C10—C11—C8	178.98 (13)
O2—N5—C13—C14	−0.1 (2)	C15—C10—C11—C12	−0.5 (2)
O3—N5—C13—C12	−0.5 (2)	N4—C10—C15—C14	179.89 (14)
O3—N5—C13—C14	179.53 (16)	C11—C10—C15—C14	0.2 (2)
N1—C1—C2—C3	178.66 (16)	C8—C11—C12—C13	−178.85 (14)
C6—C1—C2—C3	−0.3 (3)	C10—C11—C12—C13	0.5 (2)
N1—C1—C6—C5	−178.74 (15)	C11—C12—C13—N5	179.80 (13)
C2—C1—C6—C5	0.3 (2)	C11—C12—C13—C14	−0.2 (2)
C1—C2—C3—F1	−179.61 (16)	N5—C13—C14—C15	179.91 (14)
C1—C2—C3—C4	0.3 (3)	C12—C13—C14—C15	−0.1 (2)
F1—C3—C4—C5	179.64 (17)	C13—C14—C15—C10	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3	0.86	2.18	2.6166 (17)	112
N2—H2A···O1	0.86	2.06	2.7483 (16)	136
N4—H4A···O3i	0.86	2.26	3.0073 (17)	146
C2—H2···S1	0.93	2.49	3.1674 (17)	130
C4—H4···O1ii	0.93	2.39	3.281 (2)	161
C6—H6···O2iii	0.93	2.56	3.392 (2)	149
C12—H12···O2iii	0.93	2.59	3.470 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3	0.86	2.18	2.6166 (17)	112
N2—H2A⋯O1	0.86	2.06	2.7483 (16)	136
N4—H4A⋯O3i	0.86	2.26	3.0073 (17)	146
C2—H2⋯S1	0.93	2.49	3.1674 (17)	130
C4—H4⋯O1ii	0.93	2.39	3.281 (2)	161
C6—H6⋯O2iii	0.93	2.56	3.392 (2)	149
C12—H12⋯O2iii	0.93	2.59	3.470 (2)	158

Symmetry codes: (i) ; (ii) ; (iii) .