(Z)-4-(3-Fluoro­phen­yl)-1-(5-nitro-2-oxo­indolin-3-yl­idene)thio­semicarbazide

Pervez, H.; Manzoor, N.; Yaqub, M.; Tahir, M.N.

doi:10.1107/S1600536812005053

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o670

doi:10.1107/S1600536812005053

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(Z)-4-(3-Fluorophenyl)-1-(5-nitro-2-oxoindolin-3-ylidene)thiosemicarbazide

Humayun Pervez,^a Nazia Manzoor,^a Muhammad Yaqub ^a and M. Nawaz Tahir ^b ^*

^aBahauddin Zakariya University, Department of Chemistry, Multan 60800, Pakistan, and ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 5 February 2012; accepted 5 February 2012; online 10 February 2012)

In the title compound, C₁₅H₁₀FN₅O₃S, an intramolecular N—H⋯N hydrogen bond generates an S(5) ring, whereas N—H⋯O and C—H⋯S interactions complete S(6) ring motifs. The dihedral angle between the isatin ring system and the fluorobenzene ring is 5.96 (6)° and the complete molecule is close to planar (r.m.s. deviation for all the non-H atoms = 0.112 Å). In the crystal, molecules are linked by N—H⋯O hydrogen bonds to form C(8) chains along the [100] direction and C—H⋯O interactions 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_r = 359.34
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.102
S = 1.06
3728 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812005053/hb6630sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812005053/hb6630Isup3.cml

checkCIF report

Comment top

In continuation of our earlier studies on some isatins-thiosemicarbazones (Pervez et al. 2010; Pervez, Ramzan et al., 2011; Pervez, Saira et al., 2011), we report herein the structure and synthesis of the title compound (I), (Fig. 1). When compared with the crystal structures of 1-(5-nitro-2-oxoindolin-3-ylidene)-4-o-tolylthiosemi carbazide (II) (Pervez et al., 2009) and 4-(3-fluorophenyl)-1-(2-oxoindolin-3-yl-idene)thiosemicarbazides (III) (Ramzan et al., 2010), it can be noticed that it differs from (II) by the presence of fluoro function at position-3 instead of methyl at position-2 of the phenyl ring attached to N of the thiosemicarbazone moiety and from (III) by the presence of nitro substituent at position-5 of the isatin scaffold.

In (I) the fluoro-phenyl group A (C1–C6/F1), thiosemicarbazone moiety B (N1/C7/S1/N2/N3) and 5-nitro-1,3-dihydro-2H-indol-2-one group C (C8–C15/N3–N5/O1–O3) are planar with r. m. s. deviations of 0.0019, 0.0245 and 0.0071 Å, respectively. The dihedral angle between A/B, A/C and B/C is 8.67 (7)°, 5.96 (6)° and 4.35 (5)°, respectively. Due to intramolecular H-bondings of N—H···O, N—H···N and C—H···S types (Table 1, Fig. 1), S(6), S(5) and S(6) ring motifs (Bernstein et al., 1995), respectively are formed. The molecules form C(8) chains (Bernstein et al., 1995) due to intermolecular H-bondings of N—H···O type (Table 1, Fig. 2) along [100] direction, where O-atom is of nitro and N–H is of 5-nitro-1,3-dihydro-2H -indol-2-one. The polymeric chains are connected throuh C—H···O bonds to form three-dimensional network (Table 1, Fig. 2).

Related literature top

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 top

To a hot solution of 5-nitroisatin (0.48 g, 2.5 mmol) in 50% aqueous ethanol (30 ml) containing a catalytic quantity (3–4 drops) of glacial acetic acid was added 3-fluorophenythiosemicarbazide (0.46 g, 2.5 mmol) dissolved in ethanol (10 ml) and the reaction mixture was refluxed for 2 h. The orange crystalline solid formed during refluxing was collected by suction filtration. Thorough washing with hot aqueous ethanol provided the title compound (I) in pure form (0.77 g, 86%), m.p. 511 K. Orange prisms were grown in ethyl acetate-petroleum ether by diffusion method.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. The dotted lines indicate the intra-molecular H-bondings.
	Fig. 2. Packing diagram of the title compound (PLATON: Spek, 2009) showing that molecules form one dimensional polymeric chains along [100] and are interlinked.

(Z)-4-(3-Fluorophenyl)-1-(5-nitro-2-oxoindolin-3- ylidene)thiosemicarbazide top

Crystal data top

C₁₅H₁₀FN₅O₃S	F(000) = 1472
M_r = 359.34	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.045P)² + 1.1466P] where P = (F_o² + 2F_c²)/3
3728 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₅H₁₀FN₅O₃S	V = 3003.04 (13) Å³
M_r = 359.34	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 18.2485 (5) Å	µ = 0.26 mm⁻¹
b = 8.8043 (2) Å	T = 296 K
c = 18.6913 (5) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3728 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3101 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.966	R_int = 0.027
53231 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
3728 reflections	Δρ_min = −0.28 e Å⁻³
226 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, y, −z+1/2; (ii) x+1/2, −y+3/2, −z; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀FN₅O₃S
M_r	359.34
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	18.2485 (5), 8.8043 (2), 18.6913 (5)
V (Å³)	3003.04 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.957, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	53231, 3728, 3101
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.102, 1.06
No. of reflections	3728
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, y, −z+1/2; (ii) x+1/2, −y+3/2, −z; (iii) −x+1, y+1/2, −z+1/2.

Acknowledgements

We acknowledge partial funding of this research work and the award of an Indigenous PhD scholarship to NM by the Higher Education Commission, Islamabad, Pakistan.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Pervez, H., Manzoor, N., Yaqub, M., Khan, A., Khan, K. M., Nasim, F. H. & Choudhary, M. I. (2010). Lett. Drug Des. Discov. 7, 102–108. CrossRef CAS Google Scholar
Pervez, H., Ramzan, M., Yaqub, M. & Khan, K. M. (2011). Lett. Drug Des. Discov. 8, 452–458. CrossRef CAS Google Scholar
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Volume 68| Part 3| March 2012| Page o670

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(Z)-4-(3-Fluoro­phen­yl)-1-(5-nitro-2-oxo­indolin-3-yl­­idene)thio­semicarbazide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Z)-4-(3-Fluorophenyl)-1-(5-nitro-2-oxoindolin-3-ylidene)thiosemicarbazide