4-(2-Fluoro­phen­yl)-1-(2-oxoindolin-3-yl­idene)thio­semicarbazide

Pervez, H.; Yaqub, M.; Ramzan, M.; Iqbal, M.S.; Tahir, M.N.

doi:10.1107/S1600536810011682

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1018

https://doi.org/10.1107/S1600536810011682

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4-(2-Fluorophenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide

Humayun Pervez,^a Muhammad Yaqub,^a Muhammad Ramzan,^a Mohammad S. Iqbal ^b and M. Nawaz Tahir ^c ^*

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, ^bDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 26 March 2010; accepted 28 March 2010; online 2 April 2010)

The title compound, C₁₅H₁₁FN₄OS, is almost planar, the dihedral angle between the aromatic ring systems being 5.00 (13)°. The conformation is stabilized by intramolecular N—H⋯N and N—H⋯O hydrogen bonds, which generate S(5) and S(6) rings, respectively. N—H⋯F and C—H⋯S interactions also occur. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur, generating R₂²(8) loops.

Related literature

For related structures and medicinal background, see: Pervez et al. (2009 , 2010 ). For graph-set theory, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₁FN₄OS
M_r = 314.34
Monoclinic, P 2₁ /c
a = 5.7646 (3) Å
b = 18.4939 (12) Å
c = 13.6772 (8) Å
β = 91.212 (3)°
V = 1457.80 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.30 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.963, T_max = 0.971
11407 measured reflections
2626 independent reflections
1437 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.114
S = 0.96
2626 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.07	2.912 (3)	164
N3—H3⋯O1	0.86	2.08	2.762 (3)	135
N4—H4A⋯F1	0.86	2.21	2.613 (2)	109
N4—H4A⋯N2	0.86	2.13	2.585 (3)	113
C15—H15⋯S1	0.93	2.56	3.216 (3)	128
Symmetry code: (i) -x+2, -y, -z.

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: https://doi.org/10.1107/S1600536810011682/hb5381sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810011682/hb5381Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of N⁴-arylsubstituted isatins-3-thiosemecarbazones with certain medicinal applications (Pervez et al., 2009, 2010), we now report the synthesis and crystal structure of the title compound (I, Fig. 1).

The crystal structure of (II) i.e. 1-(5-nitro-2-oxoindolino-3-ylidene)- 4-o-tolylthiosemicarbazide methanol monosolvate (Pervez et al., 2009) has been published. The title compound (I) differs from (II) due to the absence of nitro function at position-5 of the isatin scaffold and presence of fluoro instead of methyl group at position-2 of the phenyl ring substituted at N⁴ of the thiosemicarbazone moiety. In (I), the 2-oxoindolin A (C1–C8/N1/O1), thiosemicarbazide B (N2/N3/C9/S1/N4) and the 2-fluorophenyl C (C10—C15/F1) are planar with maximum r. m. s. deviations of 0.0289, 0.0261 and 0.0056 Å, respectively. Due to intramolecular H-bondings (Table 1, Fig. 1), two S(5) and two S(6) (Bernstein et al., 1995) ring motifs are formed. The molecules are dimerised due to intermolecular H-bonding of N—H···O type with R₂²(8) ring motifs.

Related literature top

For related structures and medicinal background, see: Pervez et al. (2009, 2010). For graph-set theory, see: Bernstein et al. (1995).

Experimental top

To a hot solution of isatin (0.74 g, 5.0 mmol) in ethanol (10 ml) containing a few drops of glacial acetic acid was added 4-o -fluorophenylthiosemicarbazide (0.93 g, 5.0 mmol) dissolved in ethanol (10 ml) under stirring. The reaction mixture was then heated under reflux for 2 h. The yellow crystalline solid formed during refluxing was collected by suction filtration. Thorough washing with hot ethanol followed by ether furnished the target compound (I) in pure form (1.20 g, 76 %), m.p. 505-507 K (d). The dark yellow needles of (I) were grown in ethyl acetate-petroleum ether (1:5) system by diffusion method at room temperature.

Structure description top

For related structures and medicinal background, see: Pervez et al. (2009, 2010). For graph-set theory, see: Bernstein et al. (1995).

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 (I) with ellipsoids drawn at the 50% probability level. The dotted lines indicate the intramolecular H-bonds.
	Fig. 2. The partial packing of (I), which shows that molecules form inversion dimers.

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

Crystal data top

C₁₅H₁₁FN₄OS	F(000) = 648
M_r = 314.34	D_x = 1.432 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2626 reflections
a = 5.7646 (3) Å	θ = 3.5–25.3°
b = 18.4939 (12) Å	µ = 0.24 mm⁻¹
c = 13.6772 (8) Å	T = 296 K
β = 91.212 (3)°	Needle, dark yellow
V = 1457.80 (15) Å³	0.30 × 0.14 × 0.12 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2626 independent reflections
Radiation source: fine-focus sealed tube	1437 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
Detector resolution: 7.80 pixels mm^-1	θ_max = 25.3°, θ_min = 3.5°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −21→22
T_min = 0.963, T_max = 0.971	l = −16→16
11407 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0467P)²] where P = (F_o² + 2F_c²)/3
2626 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₅H₁₁FN₄OS	V = 1457.80 (15) Å³
M_r = 314.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.7646 (3) Å	µ = 0.24 mm⁻¹
b = 18.4939 (12) Å	T = 296 K
c = 13.6772 (8) Å	0.30 × 0.14 × 0.12 mm
β = 91.212 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2626 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1437 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.971	R_int = 0.068
11407 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 0.96	Δρ_max = 0.15 e Å⁻³
2626 reflections	Δρ_min = −0.22 e Å⁻³
199 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 esds 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	0.09191 (15)	0.20047 (5)	0.00689 (6)	0.0742 (3)
F1	−0.0601 (3)	0.14317 (12)	0.37578 (11)	0.0911 (9)
O1	0.7157 (3)	0.04818 (11)	0.01234 (13)	0.0575 (8)
N1	0.9081 (4)	−0.02584 (13)	0.12316 (16)	0.0547 (9)
N2	0.4000 (4)	0.06836 (12)	0.18384 (15)	0.0489 (8)
N3	0.3340 (4)	0.10541 (12)	0.10344 (15)	0.0510 (8)
N4	0.0393 (3)	0.15113 (12)	0.19057 (14)	0.0499 (8)
C1	0.5848 (5)	0.02916 (15)	0.17922 (19)	0.0474 (10)
C2	0.7385 (5)	0.01971 (16)	0.0932 (2)	0.0494 (11)
C3	0.8851 (5)	−0.04562 (15)	0.2217 (2)	0.0513 (10)
C4	1.0273 (5)	−0.08819 (17)	0.2785 (2)	0.0696 (12)
C5	0.9689 (6)	−0.09758 (19)	0.3747 (3)	0.0803 (14)
C6	0.7757 (6)	−0.06518 (19)	0.4128 (2)	0.0774 (15)
C7	0.6305 (5)	−0.02238 (17)	0.3550 (2)	0.0658 (11)
C8	0.6871 (4)	−0.01264 (15)	0.25825 (19)	0.0494 (10)
C9	0.1480 (5)	0.15218 (15)	0.10471 (18)	0.0486 (10)
C10	−0.1520 (4)	0.19126 (15)	0.22268 (19)	0.0479 (10)
C11	−0.2029 (5)	0.18597 (18)	0.3198 (2)	0.0626 (11)
C12	−0.3861 (6)	0.2210 (2)	0.3614 (3)	0.0864 (14)
C13	−0.5248 (6)	0.2633 (2)	0.3026 (3)	0.0849 (16)
C14	−0.4818 (5)	0.26920 (18)	0.2062 (3)	0.0743 (14)
C15	−0.2977 (5)	0.23337 (16)	0.1658 (2)	0.0623 (11)
H1	1.01726	−0.04097	0.08643	0.0657*
H3	0.40914	0.09984	0.05030	0.0611*
H4	1.15840	−0.10996	0.25313	0.0834*
H4A	0.09573	0.12107	0.23275	0.0598*
H5	1.06218	−0.12647	0.41499	0.0960*
H6	0.74193	−0.07212	0.47828	0.0929*
H7	0.49911	−0.00091	0.38065	0.0791*
H12	−0.41496	0.21619	0.42776	0.1037*
H13	−0.64912	0.28809	0.32902	0.1015*
H14	−0.57770	0.29779	0.16668	0.0892*
H15	−0.27161	0.23771	0.09919	0.0747*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0779 (6)	0.0878 (7)	0.0577 (5)	0.0167 (5)	0.0193 (4)	0.0148 (5)
F1	0.0833 (14)	0.1408 (19)	0.0495 (10)	0.0171 (13)	0.0103 (9)	−0.0024 (11)
O1	0.0453 (12)	0.0735 (15)	0.0543 (12)	0.0021 (10)	0.0167 (9)	−0.0014 (11)
N1	0.0398 (14)	0.0640 (17)	0.0610 (15)	0.0076 (12)	0.0148 (11)	−0.0042 (13)
N2	0.0410 (14)	0.0541 (15)	0.0519 (14)	0.0019 (12)	0.0100 (11)	−0.0051 (12)
N3	0.0481 (14)	0.0577 (16)	0.0477 (14)	0.0049 (12)	0.0153 (11)	−0.0039 (12)
N4	0.0460 (14)	0.0585 (16)	0.0455 (13)	0.0098 (12)	0.0118 (11)	−0.0016 (11)
C1	0.0397 (16)	0.0486 (18)	0.0544 (17)	−0.0033 (14)	0.0127 (13)	−0.0092 (14)
C2	0.0399 (17)	0.055 (2)	0.0537 (18)	−0.0072 (15)	0.0124 (13)	−0.0104 (15)
C3	0.0417 (17)	0.0550 (19)	0.0574 (18)	0.0009 (15)	0.0072 (14)	−0.0036 (16)
C4	0.054 (2)	0.076 (2)	0.079 (2)	0.0149 (18)	0.0073 (17)	0.0046 (19)
C5	0.075 (2)	0.089 (3)	0.077 (2)	0.017 (2)	0.0008 (19)	0.012 (2)
C6	0.086 (3)	0.090 (3)	0.0564 (19)	0.010 (2)	0.0068 (18)	0.0090 (19)
C7	0.065 (2)	0.077 (2)	0.0558 (19)	0.0075 (19)	0.0142 (16)	−0.0024 (17)
C8	0.0425 (17)	0.0527 (19)	0.0532 (17)	0.0001 (14)	0.0055 (13)	−0.0062 (15)
C9	0.0448 (17)	0.0512 (18)	0.0504 (16)	−0.0002 (15)	0.0124 (13)	−0.0052 (14)
C10	0.0404 (16)	0.0517 (19)	0.0518 (17)	−0.0038 (15)	0.0073 (13)	−0.0137 (14)
C11	0.0508 (19)	0.085 (2)	0.0519 (18)	0.0027 (18)	0.0005 (15)	−0.0134 (17)
C12	0.065 (2)	0.131 (3)	0.064 (2)	0.001 (2)	0.0214 (18)	−0.036 (2)
C13	0.049 (2)	0.106 (3)	0.100 (3)	0.008 (2)	0.010 (2)	−0.044 (2)
C14	0.053 (2)	0.075 (2)	0.095 (3)	0.0098 (18)	0.0041 (18)	−0.016 (2)
C15	0.0504 (18)	0.069 (2)	0.068 (2)	0.0058 (17)	0.0099 (15)	−0.0038 (17)

Geometric parameters (Å, º) top

S1—C9	1.635 (3)	C5—C6	1.377 (5)
F1—C11	1.365 (4)	C6—C7	1.387 (4)
O1—C2	1.229 (3)	C7—C8	1.381 (4)
N1—C2	1.348 (4)	C10—C15	1.375 (4)
N1—C3	1.406 (4)	C10—C11	1.370 (4)
N2—N3	1.344 (3)	C11—C12	1.373 (5)
N2—C1	1.291 (4)	C12—C13	1.368 (5)
N3—C9	1.378 (4)	C13—C14	1.351 (6)
N4—C9	1.343 (3)	C14—C15	1.377 (4)
N4—C10	1.407 (3)	C4—H4	0.9300
N1—H1	0.8600	C5—H5	0.9300
N3—H3	0.8600	C6—H6	0.9300
N4—H4A	0.8600	C7—H7	0.9300
C1—C8	1.445 (4)	C12—H12	0.9300
C1—C2	1.498 (4)	C13—H13	0.9300
C3—C8	1.396 (4)	C14—H14	0.9300
C3—C4	1.367 (4)	C15—H15	0.9300
C4—C5	1.376 (5)

S1···C15	3.216 (3)	C9···C2^vi	3.403 (4)
S1···C13ⁱ	3.661 (4)	C9···C14ⁱⁱⁱ	3.323 (4)
S1···C11ⁱⁱ	3.696 (3)	C9···O1^vi	3.372 (3)
S1···C12ⁱⁱ	3.665 (4)	C10···C1^vi	3.407 (4)
S1···H15	2.5600	C11···S1^vii	3.696 (3)
S1···H13ⁱ	2.8900	C12···S1^vii	3.665 (4)
F1···N4	2.613 (2)	C13···S1^viii	3.661 (4)
F1···H4A	2.2100	C14···C9^vi	3.323 (4)
O1···N2	3.022 (3)	C15···N3^vi	3.280 (4)
O1···N3	2.762 (3)	C15···S1	3.216 (3)
O1···C9ⁱⁱⁱ	3.372 (3)	C2···H3	2.4700
O1···N3^iv	3.262 (3)	C2···H3^iv	3.0600
O1···O1^iv	3.072 (3)	C2···H1^v	2.8800
O1···N1^v	2.912 (3)	C5···H14^ix	3.0200
O1···C2^iv	3.218 (3)	C6···H14^ix	2.9800
O1···H3	2.0800	C9···H15	2.8900
O1···H1^v	2.0700	C14···H4^x	2.9600
N1···O1^v	2.912 (3)	H1···O1^v	2.0700
N2···O1	3.022 (3)	H1···C2^v	2.8800
N2···N4	2.585 (3)	H3···O1	2.0800
N3···O1^iv	3.262 (3)	H3···C2	2.4700
N3···O1	2.762 (3)	H3···C2^iv	3.0600
N3···C15ⁱⁱⁱ	3.280 (4)	H4···C14^xi	2.9600
N4···C2^vi	3.254 (4)	H4A···F1	2.2100
N4···F1	2.613 (2)	H4A···N2	2.1300
N4···N2	2.585 (3)	H13···S1^viii	2.8900
N2···H4A	2.1300	H14···C5^xii	3.0200
C1···C10ⁱⁱⁱ	3.407 (4)	H14···C6^xii	2.9800
C2···N4ⁱⁱⁱ	3.254 (4)	H15···S1	2.5600
C2···C9ⁱⁱⁱ	3.403 (4)	H15···C9	2.8900
C2···O1^iv	3.218 (3)

C2—N1—C3	111.8 (2)	S1—C9—N4	129.5 (2)
N3—N2—C1	117.8 (2)	C11—C10—C15	116.6 (2)
N2—N3—C9	121.1 (2)	N4—C10—C15	126.6 (2)
C9—N4—C10	130.4 (2)	N4—C10—C11	116.8 (2)
C3—N1—H1	124.00	C10—C11—C12	123.4 (3)
C2—N1—H1	124.00	F1—C11—C10	116.5 (2)
N2—N3—H3	119.00	F1—C11—C12	120.1 (3)
C9—N3—H3	119.00	C11—C12—C13	118.1 (4)
C10—N4—H4A	115.00	C12—C13—C14	120.2 (3)
C9—N4—H4A	115.00	C13—C14—C15	120.8 (3)
N2—C1—C2	127.3 (2)	C10—C15—C14	120.8 (3)
C2—C1—C8	106.6 (2)	C3—C4—H4	121.00
N2—C1—C8	126.0 (2)	C5—C4—H4	121.00
N1—C2—C1	105.8 (2)	C4—C5—H5	119.00
O1—C2—N1	127.2 (3)	C6—C5—H5	119.00
O1—C2—C1	127.1 (3)	C5—C6—H6	119.00
N1—C3—C4	128.9 (3)	C7—C6—H6	119.00
N1—C3—C8	108.9 (2)	C6—C7—H7	121.00
C4—C3—C8	122.2 (3)	C8—C7—H7	121.00
C3—C4—C5	117.4 (3)	C11—C12—H12	121.00
C4—C5—C6	121.6 (3)	C13—C12—H12	121.00
C5—C6—C7	121.1 (3)	C12—C13—H13	120.00
C6—C7—C8	117.9 (3)	C14—C13—H13	120.00
C1—C8—C3	106.9 (2)	C13—C14—H14	120.00
C3—C8—C7	119.8 (2)	C15—C14—H14	120.00
C1—C8—C7	133.3 (2)	C10—C15—H15	120.00
S1—C9—N3	118.23 (19)	C14—C15—H15	120.00
N3—C9—N4	112.3 (2)

C3—N1—C2—O1	177.5 (3)	C8—C3—C4—C5	−0.2 (5)
C3—N1—C2—C1	−1.8 (3)	N1—C3—C8—C1	−0.2 (3)
C2—N1—C3—C4	−177.2 (3)	N1—C3—C8—C7	−178.3 (3)
C2—N1—C3—C8	1.3 (3)	C4—C3—C8—C1	178.5 (3)
C1—N2—N3—C9	−175.5 (3)	C4—C3—C8—C7	0.3 (4)
N3—N2—C1—C2	0.0 (4)	C3—C4—C5—C6	−0.4 (5)
N3—N2—C1—C8	178.0 (2)	C4—C5—C6—C7	0.8 (5)
N2—N3—C9—S1	174.9 (2)	C5—C6—C7—C8	−0.7 (5)
N2—N3—C9—N4	−4.4 (4)	C6—C7—C8—C1	−177.4 (3)
C10—N4—C9—S1	−0.8 (4)	C6—C7—C8—C3	0.1 (4)
C10—N4—C9—N3	178.3 (2)	N4—C10—C11—F1	1.1 (4)
C9—N4—C10—C11	−170.6 (3)	N4—C10—C11—C12	−179.0 (3)
C9—N4—C10—C15	11.8 (4)	C15—C10—C11—F1	179.0 (3)
N2—C1—C2—O1	0.6 (5)	C15—C10—C11—C12	−1.1 (5)
N2—C1—C2—N1	180.0 (3)	N4—C10—C15—C14	179.0 (3)
C8—C1—C2—O1	−177.7 (3)	C11—C10—C15—C14	1.3 (4)
C8—C1—C2—N1	1.7 (3)	F1—C11—C12—C13	−180.0 (3)
N2—C1—C8—C3	−179.2 (3)	C10—C11—C12—C13	0.1 (5)
N2—C1—C8—C7	−1.5 (5)	C11—C12—C13—C14	0.7 (5)
C2—C1—C8—C3	−0.9 (3)	C12—C13—C14—C15	−0.5 (5)
C2—C1—C8—C7	176.9 (3)	C13—C14—C15—C10	−0.6 (5)
N1—C3—C4—C5	178.1 (3)

Symmetry codes: (i) x+1, −y+1/2, z−1/2; (ii) x, −y+1/2, z−1/2; (iii) x+1, y, z; (iv) −x+1, −y, −z; (v) −x+2, −y, −z; (vi) x−1, y, z; (vii) x, −y+1/2, z+1/2; (viii) x−1, −y+1/2, z+1/2; (ix) −x, y−1/2, −z+1/2; (x) −x+1, y+1/2, −z+1/2; (xi) −x+1, y−1/2, −z+1/2; (xii) −x, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^v	0.86	2.07	2.912 (3)	164
N3—H3···O1	0.86	2.08	2.762 (3)	135
N4—H4A···F1	0.86	2.21	2.613 (2)	109
N4—H4A···N2	0.86	2.13	2.585 (3)	113
C15—H15···S1	0.93	2.56	3.216 (3)	128

Symmetry code: (v) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁FN₄OS
M_r	314.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.7646 (3), 18.4939 (12), 13.6772 (8)
β (°)	91.212 (3)
V (Å³)	1457.80 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.14 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.963, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	11407, 2626, 1437
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.114, 0.96
No. of reflections	2626
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.22

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···O1ⁱ	0.86	2.07	2.912 (3)	164
N3—H3···O1	0.86	2.08	2.762 (3)	135
N4—H4A···F1	0.86	2.21	2.613 (2)	109
N4—H4A···N2	0.86	2.13	2.585 (3)	113
C15—H15···S1	0.93	2.56	3.216 (3)	128

Symmetry code: (i) −x+2, −y, −z.

Acknowledgements

HP, MY and MR wish to acknowledge partial financial assistance given by the MoST, Government of Pakistan, under Projects for the Strengthening of S&T Education in Universities (Project No. P&D/S&T/2001/231).

References

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