4-[(E)-(4-Fluoro­benzyl­idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione

Devarajegowda, H.C.; Jeyaseelan, S.; Sathishkumar, R.; D'souza, A.S.; D'souza, A.

doi:10.1107/S1600536812019174

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1607

doi:10.1107/S1600536812019174

Open

access

4-[(E)-(4-Fluorobenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione

H. C. Devarajegowda,^a ^* S. Jeyaseelan,^a R. Sathishkumar,^b Agnes Sylvia D'souza ^c and Alphonsus D'souza ^c

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, Karnataka, India, and ^cDepartment of Chemistry, St. Philomena's College, Mysore 570 015, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 26 March 2012; accepted 28 April 2012; online 5 May 2012)

In the asymmetric unit of the title compound, C₁₀H₉FN₄S, there are two independent molecules in which the dihedral angles between the 1,2,4-triazole and benzene rings are 36.85 (10) and 7.81 (10)°. In the crystal, N—H⋯S interactions link pairs of independent molecules into dimers. There are also π–π interactions between the triazole and benzene rings of inversion-related pairs of the more planar molecule [centroid–centroid distance = 3.6430 (13) Å].

Related literature

For background information on the properties and uses of chalcone derivatives, see: Temple (1981 ); Holla et al. (1998 ); Heidelberger et al. (1957 ); Andersson & MacGowan (2003 ). For a related structure, see: Devarajegowda et al. (2010 ).

Experimental

Crystal data

C₁₀H₉FN₄S
M_r = 236.27
Triclinic, $[P \overline 1]$
a = 9.0048 (19) Å
b = 10.811 (2) Å
c = 12.729 (3) Å
α = 101.205 (3)°
β = 103.899 (3)°
γ = 112.376 (3)°
V = 1054.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 293 K
0.52 × 0.24 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.77, T_max = 1.00
9923 measured reflections
3698 independent reflections
3383 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.085
S = 1.05
3698 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.30 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
N3A—H3A⋯S1B	0.86	2.45	3.2840 (18)	164
N3B—H3B⋯S1A	0.86	2.51	3.3691 (18)	172

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812019174/pk2403sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019174/pk2403Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019174/pk2403Isup3.cml

checkCIF report

Comment top

4-Amino-5-mercapto-1,2,4-triazoles are the starting materials for the synthesis of a wide variety of heterocyclic derivatives which are of great importance in medicinal chemistry (Temple, 1981). Many Schiff & Mannich bases derived from 1,2,4-triazoles possess protozoacidal and bactericidal activities (Holla et al., 1998). Furthermore, fluorinated heterocycles have been shown to exhibit a wide variety of biocidal activities. Compounds such as fluorouracil and fluoroquinolone etc. have been used as anticancer agents and antibiotics respectively (Heidelberger et al., 1957; Andersson & MacGowan, 2003).

The asymmetric unit of crystals of 4-{[(1E)-(4-fluorophenyl)methylene] amino}-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C₁₀H₉F N₄S, contain two crystallographically independent molecules (Fig. 1). The 1,2,4 triazole rings (N3A,N4A,N5A,C8A,C9A and (N3B,N4B,N5B,C8B,C9B) are not coplanar with their respective benzene ring (C11A—C16A) and (C11B—C16B) systems; the dihedral angle between the two planes being 36.85 (10)° and 7.81 (10)° in the two molecules. In the crystal, N3A—H3A···S1B and N3B—H3B···S1A interactions link pairs of inequivalent molecules into dimers (Table 1.). Finally, π-π interactions between inversion-related pairs of the more planar molecule occur between the triazole (N3B,N4B,N5B,C8B,C9B) and benzene (C11B—C16B) rings [centroid-centroid distance = 3.6430 (13) Å], which stabilize the crystal packing (Fig. 2).

Related literature top

For background information on the properties and uses of chalcone derivatives, see: Temple (1981); Holla et al. (1998); Heidelberger et al. (1957); Andersson & MacGowan (2003). For a related structure, see: Devarajegowda et al. (2010).

Experimental top

An equimolar mixture of the triazole (1; 0.02 mol) and 4-fluorobenzaldehyde (0.02 mol) in absolute ethanol (30 ml) was refluxed with concentrated H₂SO₄ (0.5 ml) for 1–2 hrs. On cooling the reaction mixture, the solid product was separated and re-crystallized using ethanol as solvent.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The packing of the molecules showing the formation of hydrogen bonds that link inequivalent molecules into dimers via N3A—H3A···S1B and N3A—H3A···S1B.

4-[(E)-(4-Fluorobenzylidene)amino]-3-methyl-1H-1,2,4-triazole- 5(4H)-thione top

Crystal data top

C₁₀H₉FN₄S	Z = 4
M_r = 236.27	F(000) = 488
Triclinic, P1	D_x = 1.488 Mg m⁻³
Hall symbol: -P 1	Melting point: 441 K
a = 9.0048 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.811 (2) Å	Cell parameters from 3698 reflections
c = 12.729 (3) Å	θ = 1.7–25.0°
α = 101.205 (3)°	µ = 0.30 mm⁻¹
β = 103.899 (3)°	T = 293 K
γ = 112.376 (3)°	Plate, colourless
V = 1054.4 (4) Å³	0.52 × 0.24 × 0.13 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3698 independent reflections
Radiation source: fine-focus sealed tube	3383 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω and ϕ scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −10→10
T_min = 0.77, T_max = 1.00	k = −12→12
9923 measured reflections	l = −15→15

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0428P)² + 0.5511P] where P = (F_o² + 2F_c²)/3
3698 reflections	(Δ/σ)_max = 0.001
291 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₀H₉FN₄S	γ = 112.376 (3)°
M_r = 236.27	V = 1054.4 (4) Å³
Triclinic, P1	Z = 4
a = 9.0048 (19) Å	Mo Kα radiation
b = 10.811 (2) Å	µ = 0.30 mm⁻¹
c = 12.729 (3) Å	T = 293 K
α = 101.205 (3)°	0.52 × 0.24 × 0.13 mm
β = 103.899 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3698 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	3383 reflections with I > 2σ(I)
T_min = 0.77, T_max = 1.00	R_int = 0.017
9923 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.05	Δρ_max = 0.30 e Å⁻³
3698 reflections	Δρ_min = −0.28 e Å⁻³
291 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

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 > 2σ(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
S1A	0.23713 (5)	0.62340 (4)	0.35429 (3)	0.01697 (12)
F2A	1.06962 (13)	0.90655 (11)	0.94413 (8)	0.0227 (2)
N4A	0.40671 (18)	0.90351 (15)	0.20331 (12)	0.0173 (3)
N3A	0.29189 (18)	0.78138 (15)	0.21256 (12)	0.0156 (3)
H3A	0.1939	0.7264	0.1603	0.019*
N5A	0.50787 (17)	0.86716 (14)	0.36491 (11)	0.0143 (3)
N6A	0.62298 (17)	0.90901 (15)	0.47624 (11)	0.0158 (3)
C7A	0.6964 (2)	1.08701 (19)	0.33309 (15)	0.0229 (4)
H7A1	0.6894	1.1325	0.2756	0.034*
H7A2	0.7920	1.0658	0.3420	0.034*
H7A3	0.7112	1.1486	0.4042	0.034*
C8A	0.5365 (2)	0.95448 (18)	0.29812 (14)	0.0168 (4)
C9A	0.3462 (2)	0.75585 (17)	0.31005 (14)	0.0137 (3)
C10A	0.6362 (2)	0.80838 (17)	0.51028 (14)	0.0147 (3)
H10A	0.5724	0.7158	0.4617	0.018*
C11A	0.7512 (2)	0.83788 (17)	0.62529 (14)	0.0141 (3)
C12A	0.7622 (2)	0.72535 (18)	0.65853 (14)	0.0156 (4)
H12A	0.6968	0.6341	0.6078	0.019*
C13A	0.8693 (2)	0.74710 (18)	0.76628 (14)	0.0164 (4)
H13A	0.8764	0.6720	0.7886	0.020*
C14A	0.9647 (2)	0.88390 (18)	0.83872 (14)	0.0168 (4)
C15A	0.9588 (2)	0.99895 (18)	0.80954 (14)	0.0188 (4)
H15A	1.0257	1.0899	0.8607	0.023*
C16A	0.8504 (2)	0.97526 (18)	0.70181 (14)	0.0166 (4)
H16A	0.8437	1.0510	0.6804	0.020*
S1B	−0.10121 (5)	0.62370 (4)	0.02884 (3)	0.01602 (12)
F2B	−0.99250 (12)	0.36565 (11)	−0.53412 (8)	0.0211 (2)
N3B	−0.14587 (17)	0.43278 (14)	0.14306 (12)	0.0154 (3)
H3B	−0.0436	0.4801	0.1919	0.018*
N4B	−0.26081 (18)	0.30629 (15)	0.14576 (12)	0.0167 (3)
N5B	−0.37235 (17)	0.36840 (14)	0.00279 (11)	0.0134 (3)
N6B	−0.50533 (17)	0.34307 (15)	−0.09421 (11)	0.0154 (3)
C7B	−0.5645 (2)	0.14351 (18)	0.02702 (15)	0.0201 (4)
H7B1	−0.5561	0.0904	0.0786	0.030*
H7B2	−0.5940	0.0854	−0.0494	0.030*
H7B3	−0.6513	0.1734	0.0307	0.030*
C8B	−0.3976 (2)	0.26907 (18)	0.05969 (14)	0.0154 (4)
C9B	−0.2066 (2)	0.47588 (17)	0.05816 (13)	0.0137 (3)
C10B	−0.4876 (2)	0.43797 (18)	−0.14289 (14)	0.0157 (4)
H10B	−0.3874	0.5224	−0.1132	0.019*
C11B	−0.6245 (2)	0.41410 (18)	−0.24528 (14)	0.0152 (4)
C12B	−0.6015 (2)	0.52269 (18)	−0.29298 (14)	0.0163 (4)
H12B	−0.5009	0.6067	−0.2589	0.020*
C13B	−0.7250 (2)	0.50845 (18)	−0.39004 (14)	0.0165 (4)
H13B	−0.7092	0.5812	−0.4216	0.020*
C14B	−0.8721 (2)	0.38242 (18)	−0.43791 (13)	0.0159 (4)
C15B	−0.9013 (2)	0.27145 (18)	−0.39334 (14)	0.0175 (4)
H15B	−1.0024	0.1880	−0.4279	0.021*
C16B	−0.7764 (2)	0.28784 (18)	−0.29615 (14)	0.0162 (4)
H16B	−0.7935	0.2150	−0.2647	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.0138 (2)	0.0175 (2)	0.0161 (2)	0.00357 (18)	0.00235 (17)	0.00864 (17)
F2A	0.0208 (5)	0.0240 (6)	0.0141 (5)	0.0056 (5)	−0.0019 (4)	0.0066 (4)
N4A	0.0152 (7)	0.0167 (7)	0.0181 (7)	0.0047 (6)	0.0043 (6)	0.0086 (6)
N3A	0.0116 (7)	0.0161 (7)	0.0145 (7)	0.0036 (6)	0.0005 (6)	0.0059 (6)
N5A	0.0136 (7)	0.0137 (7)	0.0130 (7)	0.0050 (6)	0.0014 (6)	0.0055 (6)
N6A	0.0132 (7)	0.0180 (7)	0.0117 (7)	0.0048 (6)	0.0003 (6)	0.0052 (6)
C7A	0.0201 (9)	0.0191 (9)	0.0216 (9)	0.0021 (8)	0.0022 (8)	0.0105 (8)
C8A	0.0169 (9)	0.0182 (9)	0.0166 (8)	0.0080 (7)	0.0051 (7)	0.0089 (7)
C9A	0.0131 (8)	0.0153 (8)	0.0126 (8)	0.0074 (7)	0.0030 (7)	0.0041 (6)
C10A	0.0126 (8)	0.0150 (8)	0.0151 (8)	0.0045 (7)	0.0050 (7)	0.0045 (7)
C11A	0.0110 (8)	0.0176 (8)	0.0131 (8)	0.0051 (7)	0.0047 (7)	0.0055 (7)
C12A	0.0134 (8)	0.0152 (8)	0.0152 (8)	0.0047 (7)	0.0037 (7)	0.0035 (7)
C13A	0.0175 (9)	0.0167 (9)	0.0170 (8)	0.0083 (7)	0.0058 (7)	0.0086 (7)
C14A	0.0137 (8)	0.0233 (9)	0.0107 (8)	0.0060 (7)	0.0024 (7)	0.0069 (7)
C15A	0.0193 (9)	0.0157 (9)	0.0149 (8)	0.0034 (7)	0.0043 (7)	0.0023 (7)
C16A	0.0196 (9)	0.0161 (9)	0.0170 (8)	0.0088 (7)	0.0073 (7)	0.0084 (7)
S1B	0.0125 (2)	0.0161 (2)	0.0166 (2)	0.00421 (17)	0.00188 (17)	0.00781 (17)
F2B	0.0166 (5)	0.0258 (6)	0.0163 (5)	0.0081 (4)	−0.0012 (4)	0.0089 (4)
N3B	0.0105 (7)	0.0172 (7)	0.0151 (7)	0.0040 (6)	0.0015 (6)	0.0066 (6)
N4B	0.0151 (7)	0.0184 (7)	0.0168 (7)	0.0067 (6)	0.0050 (6)	0.0081 (6)
N5B	0.0114 (7)	0.0147 (7)	0.0118 (7)	0.0051 (6)	0.0013 (6)	0.0047 (6)
N6B	0.0135 (7)	0.0191 (7)	0.0119 (7)	0.0080 (6)	0.0009 (6)	0.0044 (6)
C7B	0.0181 (9)	0.0181 (9)	0.0191 (9)	0.0040 (7)	0.0028 (7)	0.0089 (7)
C8B	0.0184 (9)	0.0173 (9)	0.0136 (8)	0.0092 (7)	0.0070 (7)	0.0074 (7)
C9B	0.0132 (8)	0.0165 (8)	0.0127 (8)	0.0081 (7)	0.0043 (7)	0.0048 (7)
C10B	0.0131 (8)	0.0175 (9)	0.0150 (8)	0.0063 (7)	0.0032 (7)	0.0052 (7)
C11B	0.0142 (8)	0.0192 (9)	0.0135 (8)	0.0089 (7)	0.0047 (7)	0.0051 (7)
C12B	0.0129 (8)	0.0173 (9)	0.0154 (8)	0.0042 (7)	0.0044 (7)	0.0045 (7)
C13B	0.0186 (9)	0.0187 (9)	0.0161 (8)	0.0099 (7)	0.0069 (7)	0.0092 (7)
C14B	0.0126 (8)	0.0244 (9)	0.0106 (8)	0.0097 (7)	0.0018 (7)	0.0054 (7)
C15B	0.0135 (8)	0.0170 (9)	0.0176 (9)	0.0039 (7)	0.0037 (7)	0.0046 (7)
C16B	0.0164 (9)	0.0186 (9)	0.0158 (8)	0.0085 (7)	0.0060 (7)	0.0079 (7)

Geometric parameters (Å, º) top

S1A—C9A	1.6854 (17)	S1B—C9B	1.6855 (17)
F2A—C14A	1.3564 (19)	F2B—C14B	1.3545 (18)
N4A—C8A	1.304 (2)	N3B—C9B	1.338 (2)
N4A—N3A	1.3805 (19)	N3B—N4B	1.3785 (19)
N3A—C9A	1.341 (2)	N3B—H3B	0.8600
N3A—H3A	0.8600	N4B—C8B	1.297 (2)
N5A—C9A	1.381 (2)	N5B—C8B	1.387 (2)
N5A—C8A	1.383 (2)	N5B—C9B	1.390 (2)
N5A—N6A	1.4055 (18)	N5B—N6B	1.3935 (18)
N6A—C10A	1.282 (2)	N6B—C10B	1.277 (2)
C7A—C8A	1.482 (2)	C7B—C8B	1.484 (2)
C7A—H7A1	0.9600	C7B—H7B1	0.9600
C7A—H7A2	0.9600	C7B—H7B2	0.9600
C7A—H7A3	0.9600	C7B—H7B3	0.9600
C10A—C11A	1.468 (2)	C10B—C11B	1.463 (2)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.393 (2)	C11B—C12B	1.394 (2)
C11A—C16A	1.401 (2)	C11B—C16B	1.401 (2)
C12A—C13A	1.390 (2)	C12B—C13B	1.387 (2)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.378 (2)	C13B—C14B	1.377 (2)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.381 (2)	C14B—C15B	1.388 (2)
C15A—C16A	1.389 (2)	C15B—C16B	1.386 (2)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—H16A	0.9300	C16B—H16B	0.9300

C8A—N4A—N3A	103.69 (13)	C9B—N3B—N4B	114.48 (13)
C9A—N3A—N4A	114.26 (13)	C9B—N3B—H3B	122.8
C9A—N3A—H3A	122.9	N4B—N3B—H3B	122.8
N4A—N3A—H3A	122.9	C8B—N4B—N3B	104.14 (13)
C9A—N5A—C8A	108.36 (13)	C8B—N5B—C9B	108.24 (13)
C9A—N5A—N6A	130.31 (14)	C8B—N5B—N6B	118.40 (13)
C8A—N5A—N6A	120.57 (13)	C9B—N5B—N6B	133.34 (14)
C10A—N6A—N5A	115.20 (14)	C10B—N6B—N5B	118.87 (14)
C8A—C7A—H7A1	109.5	C8B—C7B—H7B1	109.5
C8A—C7A—H7A2	109.5	C8B—C7B—H7B2	109.5
H7A1—C7A—H7A2	109.5	H7B1—C7B—H7B2	109.5
C8A—C7A—H7A3	109.5	C8B—C7B—H7B3	109.5
H7A1—C7A—H7A3	109.5	H7B1—C7B—H7B3	109.5
H7A2—C7A—H7A3	109.5	H7B2—C7B—H7B3	109.5
N4A—C8A—N5A	110.95 (15)	N4B—C8B—N5B	110.75 (15)
N4A—C8A—C7A	126.29 (15)	N4B—C8B—C7B	126.55 (15)
N5A—C8A—C7A	122.75 (15)	N5B—C8B—C7B	122.61 (14)
N3A—C9A—N5A	102.69 (14)	N3B—C9B—N5B	102.39 (14)
N3A—C9A—S1A	127.58 (13)	N3B—C9B—S1B	127.11 (13)
N5A—C9A—S1A	129.68 (12)	N5B—C9B—S1B	130.49 (12)
N6A—C10A—C11A	120.60 (15)	N6B—C10B—C11B	120.14 (15)
N6A—C10A—H10A	119.7	N6B—C10B—H10B	119.9
C11A—C10A—H10A	119.7	C11B—C10B—H10B	119.9
C12A—C11A—C16A	119.27 (15)	C12B—C11B—C16B	119.26 (15)
C12A—C11A—C10A	118.67 (15)	C12B—C11B—C10B	117.97 (15)
C16A—C11A—C10A	122.06 (15)	C16B—C11B—C10B	122.77 (15)
C13A—C12A—C11A	121.16 (15)	C13B—C12B—C11B	121.55 (16)
C13A—C12A—H12A	119.4	C13B—C12B—H12B	119.2
C11A—C12A—H12A	119.4	C11B—C12B—H12B	119.2
C14A—C13A—C12A	117.62 (15)	C14B—C13B—C12B	117.43 (16)
C14A—C13A—H13A	121.2	C14B—C13B—H13B	121.3
C12A—C13A—H13A	121.2	C12B—C13B—H13B	121.3
F2A—C14A—C13A	118.21 (15)	F2B—C14B—C13B	118.19 (15)
F2A—C14A—C15A	118.41 (15)	F2B—C14B—C15B	118.62 (15)
C13A—C14A—C15A	123.38 (15)	C13B—C14B—C15B	123.18 (15)
C14A—C15A—C16A	118.25 (16)	C16B—C15B—C14B	118.52 (16)
C14A—C15A—H15A	120.9	C16B—C15B—H15B	120.7
C16A—C15A—H15A	120.9	C14B—C15B—H15B	120.7
C15A—C16A—C11A	120.32 (16)	C15B—C16B—C11B	120.06 (16)
C15A—C16A—H16A	119.8	C15B—C16B—H16B	120.0
C11A—C16A—H16A	119.8	C11B—C16B—H16B	120.0

C8A—N4A—N3A—C9A	0.33 (18)	C9B—N3B—N4B—C8B	0.09 (18)
C9A—N5A—N6A—C10A	42.7 (2)	C8B—N5B—N6B—C10B	175.50 (14)
C8A—N5A—N6A—C10A	−148.60 (15)	C9B—N5B—N6B—C10B	−6.8 (3)
N3A—N4A—C8A—N5A	1.13 (18)	N3B—N4B—C8B—N5B	−0.02 (18)
N3A—N4A—C8A—C7A	−179.27 (17)	N3B—N4B—C8B—C7B	−176.50 (16)
C9A—N5A—C8A—N4A	−2.17 (19)	C9B—N5B—C8B—N4B	−0.05 (19)
N6A—N5A—C8A—N4A	−173.13 (14)	N6B—N5B—C8B—N4B	178.23 (13)
C9A—N5A—C8A—C7A	178.21 (16)	C9B—N5B—C8B—C7B	176.60 (15)
N6A—N5A—C8A—C7A	7.2 (2)	N6B—N5B—C8B—C7B	−5.1 (2)
N4A—N3A—C9A—N5A	−1.58 (18)	N4B—N3B—C9B—N5B	−0.11 (17)
N4A—N3A—C9A—S1A	176.05 (12)	N4B—N3B—C9B—S1B	−179.39 (12)
C8A—N5A—C9A—N3A	2.17 (17)	C8B—N5B—C9B—N3B	0.09 (17)
N6A—N5A—C9A—N3A	171.95 (15)	N6B—N5B—C9B—N3B	−177.83 (15)
C8A—N5A—C9A—S1A	−175.39 (13)	C8B—N5B—C9B—S1B	179.34 (13)
N6A—N5A—C9A—S1A	−5.6 (3)	N6B—N5B—C9B—S1B	1.4 (3)
N5A—N6A—C10A—C11A	−179.52 (13)	N5B—N6B—C10B—C11B	179.62 (14)
N6A—C10A—C11A—C12A	−179.68 (15)	N6B—C10B—C11B—C12B	177.84 (15)
N6A—C10A—C11A—C16A	−0.1 (2)	N6B—C10B—C11B—C16B	−1.8 (3)
C16A—C11A—C12A—C13A	0.2 (2)	C16B—C11B—C12B—C13B	−0.4 (2)
C10A—C11A—C12A—C13A	179.80 (15)	C10B—C11B—C12B—C13B	179.94 (15)
C11A—C12A—C13A—C14A	−0.3 (2)	C11B—C12B—C13B—C14B	0.0 (2)
C12A—C13A—C14A—F2A	179.92 (14)	C12B—C13B—C14B—F2B	−178.64 (14)
C12A—C13A—C14A—C15A	0.0 (3)	C12B—C13B—C14B—C15B	0.3 (3)
F2A—C14A—C15A—C16A	−179.57 (14)	F2B—C14B—C15B—C16B	178.77 (14)
C13A—C14A—C15A—C16A	0.4 (3)	C13B—C14B—C15B—C16B	−0.2 (3)
C14A—C15A—C16A—C11A	−0.4 (2)	C14B—C15B—C16B—C11B	−0.2 (2)
C12A—C11A—C16A—C15A	0.1 (2)	C12B—C11B—C16B—C15B	0.5 (2)
C10A—C11A—C16A—C15A	−179.41 (15)	C10B—C11B—C16B—C15B	−179.81 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A···S1B	0.86	2.45	3.2840 (18)	164
N3B—H3B···S1A	0.86	2.51	3.3691 (18)	172

Experimental details

Crystal data
Chemical formula	C₁₀H₉FN₄S
M_r	236.27
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.0048 (19), 10.811 (2), 12.729 (3)
α, β, γ (°)	101.205 (3), 103.899 (3), 112.376 (3)
V (Å³)	1054.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.52 × 0.24 × 0.13

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.77, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	9923, 3698, 3383
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.085, 1.05
No. of reflections	3698
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.28

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A···S1B	0.86	2.4500	3.2840 (18)	164.00
N3B—H3B···S1A	0.86	2.5100	3.3691 (18)	172.00

Acknowledgements

The authors thank Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for the data collection.

References

Andersson, M. I. & MacGowan, A. P. (2003). J. Antimicrob. Chemother. 51, 1–11. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Devarajegowda, H. C., Jeyaseelan, S., Sumangala, V., Bojapoojary & Nayak, S. P. (2010). Acta Cryst. E66, o2512–o2513. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Heidelberger, C., Chaudhuri, N. K., Danneberg, P., Mooren, D., Greisbach, L., Duschinsky, R., Scnnitzer, R. J., Pleaven, E. & Scheiner, J. (1957). Nature (London), 179, 663–666. CrossRef PubMed CAS Web of Science Google Scholar
Holla, B. S., Shivananda, M. K., Shenoy, S. & Antony, G. (1998). Boll. Chim. Farm. 136, 680–685. Google Scholar
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Temple, C. (1981). The Chemistry of Heterocyclic Compounds, Vol. 37, edited by J. A. Montgomery, pp. 62–95. New York: Wiley Interscience. Google Scholar