1-(6-Fluoro-1,3-benzothia­zol-2-yl)-2-(1-phenyl­ethyl­idene)hydrazine

Fun, H.-K.; Quah, C.K.; Munirajasekhar, D.; Himaja, M.; Sarojini, B.K.

doi:10.1107/S1600536812030851

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages o2438-o2439

https://doi.org/10.1107/S1600536812030851

Open

access

1-(6-Fluoro-1,3-benzothiazol-2-yl)-2-(1-phenylethylidene)hydrazine

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § D. Munirajasekhar,^b M. Himaja ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bChemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 4 July 2012; accepted 6 July 2012; online 14 July 2012)

The asymmetric unit of the title compound, C₁₅H₁₂FN₃S, consists of two independent molecules with comparable geometries. In one molecule, the 1,3-benzothiazole ring system (r.m.s. deviation = 0.011 Å) forms a dihedral angle of 19.86 (6)° with the phenyl ring. The corresponding r.m.s. deviation and dihedral angle for the other molecule are 0.014 Å and 22.32 (6)°, respectively. In the crystal, molecules are linked via N—H⋯N, C—H⋯F and C—H⋯N hydrogen bonds into a three-dimensional network. The crystal studied was a non-merohedral twin with a refined BASF value of 0.301 (2).

Related literature

For general background to and the biological activities of benzothiazoles derivatives, see: Al-Soud et al. (2006 ); Kini et al. (2007 ); Munirajasekhar et al. (2011 ); Gurupadayya et al. (2008 ); Bowyer et al. (2007 ); Mittal et al. (2007 ); Pozas et al. (2005 ); Rana et al. (2008 ). For standard bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₅H₁₂FN₃S
M_r = 285.34
Monoclinic, P 2/c
a = 28.312 (3) Å
b = 7.2952 (7) Å
c = 13.0626 (13) Å
β = 103.151 (2)°
V = 2627.2 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.46 × 0.21 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.894, T_max = 0.965
52781 measured reflections
7411 independent reflections
7049 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.080
S = 1.06
7411 reflections
364 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H1NA⋯N1Aⁱ	0.93	1.99	2.902 (2)	165
N2B—H1NB⋯N1Bⁱⁱ	0.79	2.14	2.9184 (18)	168
C5B—H5BA⋯F1Bⁱⁱⁱ	0.95	2.51	3.310 (2)	142
C12B—H12A⋯F1A^iv	0.95	2.52	3.289 (2)	138
C12A—H12B⋯F1B^v	0.95	2.43	3.200 (2)	138
C15B—H15A⋯N1Bⁱⁱ	0.98	2.57	3.503 (2)	160
Symmetry codes: (i) $[-x+2, y, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+2, z-{\script{1\over 2}}]$ ; (iv) $[-x+2, y, -z+{\script{5\over 2}}]$ ; (v) -x+1, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812030851/rz2786sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030851/rz2786Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812030851/rz2786Isup3.cml

checkCIF report

Comment top

Benzothiazoles are very important bicyclic compounds which are of great interest because of their biological activities. The substituted benzothiazole derivatives have emerged as significant components in various diversified therapeutic applications. The literature review reveals that benzothiazoles and their derivatives show considerable activity including potent inhibition of human immunodeficiency virus type 1 (HIV-1) replication by HIV-1 protease inhibition (Al-Soud et al., 2006), antitumor (Kini et al., 2007), anthelmintic (Munirajasekhar et al., 2011) analgesic and anti-inflammatory (Gurupadayya et al., 2008), antimalarial (Bowyer et al., 2007), antifungal (Mittal et al., 2007), anticandidous activities (Pozas et al., 2005) and various CNS activities (Rana et al., 2008). The present work describes the synthesis and crystal structure of the title compound, 1-(6-fluoro1,3-benzothiazol-2-yl)-2-(1-phenylethylidene)hydrazine, which was prepared from the condensation reaction of 1-(6-fluoro1,3-benzothiazol-2-yl)hydrazine by refluxing for 2 h with acetophenone in presence of methanol.

The asymmetric unit (Fig. 1) of the title compound consists of two independent molecules (A and B), with comparable geometries. In molecule A, the 1,3-benzothiazol-2-yl ring system (S1A/N1A/C1A-C7A, r.m.s. deviation = 0.011 Å) forms a dihedral angle of 19.86 (6)° with the phenyl ring (C9A-C14A). The corresponding r.m.s. deviation and dihedral angle for molecule B are 0.014 Å and 22.32 (6)°, respectively. Bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal structure, Fig. 2, molecules are linked via intermolecular N2A–H1NA···N1A, N2B–H1NB···N1B, C5B–H5BA···F1B, C12B–H12A···F1A, C12A–H12B···F1B and C15B–H15A···N1B hydrogen bonds (Table 1) into a three-dimensional network.

Related literature top

For general background to and the biological activities of benzothiazoles derivatives, see: Al-Soud et al. (2006); Kini et al. (2007); Munirajasekhar et al. (2011); Gurupadayya et al. (2008); Bowyer et al. (2007); Mittal et al. (2007); Pozas et al. (2005); Rana et al. (2008). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 1-(6-fluoro1,3-benzothiazol-2-yl)hydrazine (1.83 g, 10 mmol) and acetophenone (1.2 g, 10 mmol) in methanol (50 mL) was refluxed at 2 h. After completion of the reaction, as monitored by TLC, the reaction mixture was poured into ice water (100 mL) whereby the crude product was precipitated as a yellow solid. The product obtained was washed with water and dried. The crude product was recrystalized from an ethylacetate/ethanol mixture (1:1 v/v). M.p.: 455-457 K.

Structure description top

For general background to and the biological activities of benzothiazoles derivatives, see: Al-Soud et al. (2006); Kini et al. (2007); Munirajasekhar et al. (2011); Gurupadayya et al. (2008); Bowyer et al. (2007); Mittal et al. (2007); Pozas et al. (2005); Rana et al. (2008). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

1-(6-Fluoro-1,3-benzothiazol-2-yl)-2-(1-phenylethylidene)hydrazine top

Crystal data top

C₁₅H₁₂FN₃S	F(000) = 1184
M_r = 285.34	D_x = 1.443 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 9959 reflections
a = 28.312 (3) Å	θ = 2.9–29.6°
b = 7.2952 (7) Å	µ = 0.25 mm⁻¹
c = 13.0626 (13) Å	T = 100 K
β = 103.151 (2)°	Block, yellow
V = 2627.2 (5) Å³	0.46 × 0.21 × 0.14 mm
Z = 8

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	7411 independent reflections
Radiation source: fine-focus sealed tube	7049 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 29.7°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −39→39
T_min = 0.894, T_max = 0.965	k = −10→10
52781 measured reflections	l = −18→18

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) = 0.080	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0333P)² + 1.4375P] where P = (F_o² + 2F_c²)/3
7411 reflections	(Δ/σ)_max = 0.002
364 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₅H₁₂FN₃S	V = 2627.2 (5) Å³
M_r = 285.34	Z = 8
Monoclinic, P2/c	Mo Kα radiation
a = 28.312 (3) Å	µ = 0.25 mm⁻¹
b = 7.2952 (7) Å	T = 100 K
c = 13.0626 (13) Å	0.46 × 0.21 × 0.14 mm
β = 103.151 (2)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	7411 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	7049 reflections with I > 2σ(I)
T_min = 0.894, T_max = 0.965	R_int = 0.036
52781 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.06	Δρ_max = 0.46 e Å⁻³
7411 reflections	Δρ_min = −0.43 e Å⁻³
364 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.972160 (13)	0.76932 (5)	1.01810 (3)	0.01518 (8)
F1A	1.12593 (4)	0.52213 (16)	1.27187 (9)	0.0279 (2)
N1A	1.02856 (5)	0.76694 (18)	0.88368 (11)	0.0153 (2)
N2A	0.94918 (4)	0.86931 (19)	0.81485 (11)	0.0164 (3)
H1NA	0.9510	0.8461	0.7457	0.020*
N3A	0.90434 (4)	0.88095 (18)	0.83979 (11)	0.0156 (2)
C1A	1.03203 (5)	0.6981 (2)	1.06242 (13)	0.0157 (3)
C2A	1.05463 (6)	0.6359 (2)	1.16183 (13)	0.0185 (3)
H2AA	1.0381	0.6291	1.2174	0.022*
C3A	1.10265 (6)	0.5845 (2)	1.17516 (13)	0.0197 (3)
C4A	1.12836 (6)	0.5918 (2)	1.09697 (14)	0.0197 (3)
H4AA	1.1615	0.5562	1.1112	0.024*
C5A	1.10515 (5)	0.6519 (2)	0.99766 (13)	0.0176 (3)
H5AA	1.1220	0.6561	0.9425	0.021*
C6A	1.05651 (5)	0.7064 (2)	0.97977 (13)	0.0142 (3)
C7A	0.98479 (5)	0.8033 (2)	0.89425 (12)	0.0141 (3)
C8A	0.86838 (5)	0.9481 (2)	0.77176 (12)	0.0151 (3)
C9A	0.82091 (5)	0.9398 (2)	0.80292 (13)	0.0154 (3)
C10A	0.77909 (5)	1.0154 (2)	0.73955 (13)	0.0190 (3)
H10B	0.7811	1.0814	0.6780	0.023*
C11A	0.73430 (5)	0.9950 (2)	0.76586 (14)	0.0224 (3)
H11B	0.7061	1.0482	0.7224	0.027*
C12A	0.73052 (6)	0.8977 (2)	0.85482 (15)	0.0222 (3)
H12B	0.6999	0.8819	0.8716	0.027*
C13A	0.77206 (6)	0.8236 (2)	0.91916 (15)	0.0219 (3)
H13B	0.7699	0.7578	0.9807	0.026*
C14A	0.81679 (5)	0.8455 (2)	0.89382 (13)	0.0180 (3)
H14B	0.8450	0.7957	0.9388	0.022*
C15A	0.87077 (6)	1.0251 (2)	0.66642 (14)	0.0212 (3)
H15D	0.9046	1.0273	0.6600	0.032*
H15E	0.8577	1.1500	0.6599	0.032*
H15F	0.8516	0.9481	0.6107	0.032*
S1B	0.530131 (12)	0.72187 (5)	1.04747 (3)	0.01352 (8)
F1B	0.37853 (3)	0.96714 (15)	1.16254 (8)	0.0242 (2)
N1B	0.47380 (4)	0.75091 (17)	0.85933 (10)	0.0135 (2)
N2B	0.55248 (4)	0.64677 (18)	0.86209 (10)	0.0154 (2)
H1NB	0.5496	0.6729	0.8024	0.018*
N3B	0.59655 (4)	0.60724 (17)	0.92759 (10)	0.0139 (2)
C1B	0.47084 (5)	0.7988 (2)	1.03672 (12)	0.0125 (3)
C2B	0.44856 (5)	0.8532 (2)	1.11663 (13)	0.0164 (3)
H2BA	0.4652	0.8500	1.1885	0.020*
C3B	0.40115 (5)	0.9118 (2)	1.08580 (13)	0.0161 (3)
C4B	0.37534 (5)	0.9174 (2)	0.98252 (13)	0.0160 (3)
H4BA	0.3425	0.9572	0.9656	0.019*
C5B	0.39812 (5)	0.8640 (2)	0.90372 (13)	0.0154 (3)
H5BA	0.3811	0.8676	0.8321	0.019*
C6B	0.44636 (5)	0.80470 (19)	0.93059 (12)	0.0125 (3)
C7B	0.51744 (5)	0.7067 (2)	0.91009 (12)	0.0131 (3)
C8B	0.62998 (5)	0.5364 (2)	0.88735 (12)	0.0143 (3)
C9B	0.67655 (5)	0.4959 (2)	0.96244 (12)	0.0133 (3)
C10B	0.71024 (5)	0.3762 (2)	0.93491 (13)	0.0181 (3)
H10A	0.7037	0.3245	0.8664	0.022*
C11B	0.75312 (5)	0.3316 (2)	1.00643 (15)	0.0222 (3)
H11A	0.7754	0.2487	0.9870	0.027*
C12B	0.76319 (5)	0.4081 (2)	1.10577 (15)	0.0223 (3)
H12A	0.7924	0.3780	1.1548	0.027*
C13B	0.73027 (6)	0.5300 (2)	1.13402 (13)	0.0208 (3)
H13A	0.7373	0.5832	1.2022	0.025*
C14B	0.68728 (5)	0.5737 (2)	1.06267 (13)	0.0173 (3)
H14A	0.6651	0.6570	1.0823	0.021*
C15B	0.62514 (6)	0.4894 (2)	0.77311 (13)	0.0192 (3)
H15A	0.5936	0.5318	0.7323	0.029*
H15B	0.6276	0.3563	0.7655	0.029*
H15C	0.6511	0.5496	0.7472	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.01302 (15)	0.01712 (18)	0.01631 (19)	0.00009 (13)	0.00523 (13)	−0.00027 (13)
F1A	0.0272 (5)	0.0317 (6)	0.0211 (5)	0.0061 (4)	−0.0024 (4)	0.0071 (5)
N1A	0.0138 (5)	0.0159 (6)	0.0158 (6)	0.0004 (5)	0.0027 (5)	0.0006 (5)
N2A	0.0130 (5)	0.0205 (6)	0.0160 (6)	0.0019 (5)	0.0040 (5)	0.0003 (5)
N3A	0.0135 (5)	0.0169 (6)	0.0166 (6)	0.0009 (4)	0.0039 (5)	−0.0002 (5)
C1A	0.0142 (6)	0.0144 (7)	0.0184 (7)	−0.0004 (5)	0.0038 (5)	0.0001 (6)
C2A	0.0204 (7)	0.0180 (7)	0.0173 (7)	−0.0005 (6)	0.0050 (6)	0.0018 (6)
C3A	0.0204 (7)	0.0177 (7)	0.0183 (8)	0.0017 (6)	−0.0012 (6)	0.0020 (6)
C4A	0.0156 (6)	0.0172 (7)	0.0248 (8)	0.0021 (5)	0.0020 (6)	−0.0002 (6)
C5A	0.0143 (6)	0.0160 (7)	0.0228 (8)	0.0007 (5)	0.0051 (6)	0.0003 (6)
C6A	0.0138 (6)	0.0122 (6)	0.0168 (7)	0.0000 (5)	0.0041 (5)	−0.0005 (5)
C7A	0.0148 (6)	0.0131 (6)	0.0148 (7)	−0.0014 (5)	0.0045 (5)	−0.0008 (5)
C8A	0.0150 (6)	0.0136 (7)	0.0167 (7)	0.0010 (5)	0.0033 (5)	−0.0021 (6)
C9A	0.0134 (6)	0.0130 (6)	0.0192 (7)	0.0010 (5)	0.0025 (5)	−0.0023 (6)
C10A	0.0177 (6)	0.0190 (7)	0.0192 (7)	0.0031 (6)	0.0017 (6)	−0.0005 (6)
C11A	0.0137 (6)	0.0231 (8)	0.0284 (9)	0.0046 (6)	0.0008 (6)	−0.0029 (7)
C12A	0.0151 (6)	0.0216 (8)	0.0310 (9)	0.0010 (6)	0.0073 (6)	−0.0037 (7)
C13A	0.0191 (7)	0.0200 (7)	0.0282 (9)	0.0011 (6)	0.0085 (6)	0.0008 (7)
C14A	0.0145 (6)	0.0176 (7)	0.0217 (8)	0.0022 (5)	0.0035 (6)	−0.0001 (6)
C15A	0.0192 (7)	0.0245 (8)	0.0204 (8)	0.0045 (6)	0.0056 (6)	0.0025 (6)
S1B	0.01062 (15)	0.01609 (17)	0.01314 (17)	0.00098 (12)	0.00124 (13)	0.00005 (13)
F1B	0.0191 (4)	0.0361 (6)	0.0192 (5)	0.0064 (4)	0.0078 (4)	−0.0052 (4)
N1B	0.0113 (5)	0.0168 (6)	0.0123 (6)	0.0002 (4)	0.0025 (4)	0.0001 (5)
N2B	0.0122 (5)	0.0198 (6)	0.0143 (6)	0.0038 (5)	0.0034 (5)	0.0009 (5)
N3B	0.0119 (5)	0.0146 (6)	0.0146 (6)	0.0007 (4)	0.0018 (4)	0.0011 (5)
C1B	0.0108 (5)	0.0133 (6)	0.0129 (6)	−0.0003 (5)	0.0016 (5)	−0.0014 (5)
C2B	0.0156 (6)	0.0201 (7)	0.0131 (7)	0.0000 (5)	0.0026 (5)	−0.0015 (6)
C3B	0.0158 (6)	0.0181 (7)	0.0161 (7)	0.0009 (5)	0.0069 (5)	−0.0027 (6)
C4B	0.0115 (6)	0.0163 (7)	0.0206 (7)	0.0016 (5)	0.0043 (5)	0.0008 (6)
C5B	0.0129 (6)	0.0165 (7)	0.0164 (7)	0.0008 (5)	0.0024 (5)	0.0012 (6)
C6B	0.0126 (6)	0.0125 (6)	0.0127 (6)	−0.0007 (5)	0.0036 (5)	0.0011 (5)
C7B	0.0130 (6)	0.0130 (6)	0.0127 (7)	−0.0006 (5)	0.0016 (5)	0.0000 (5)
C8B	0.0128 (6)	0.0146 (7)	0.0157 (7)	0.0005 (5)	0.0036 (5)	0.0016 (6)
C9B	0.0120 (6)	0.0139 (6)	0.0139 (7)	0.0003 (5)	0.0030 (5)	0.0028 (5)
C10B	0.0154 (6)	0.0175 (7)	0.0211 (8)	0.0019 (5)	0.0036 (6)	−0.0006 (6)
C11B	0.0153 (6)	0.0191 (7)	0.0313 (9)	0.0035 (5)	0.0032 (6)	0.0025 (7)
C12B	0.0154 (6)	0.0212 (8)	0.0275 (9)	−0.0008 (6)	−0.0009 (6)	0.0056 (7)
C13B	0.0189 (7)	0.0252 (8)	0.0167 (7)	−0.0023 (6)	0.0004 (6)	0.0021 (6)
C14B	0.0159 (6)	0.0200 (7)	0.0166 (7)	−0.0002 (5)	0.0047 (5)	0.0011 (6)
C15B	0.0190 (6)	0.0244 (8)	0.0140 (7)	0.0069 (6)	0.0032 (6)	−0.0016 (6)

Geometric parameters (Å, º) top

S1A—C1A	1.7414 (15)	S1B—C1B	1.7451 (15)
S1A—C7A	1.7521 (16)	S1B—C7B	1.7518 (16)
F1A—C3A	1.3632 (19)	F1B—C3B	1.3674 (17)
N1A—C7A	1.3051 (19)	N1B—C7B	1.3029 (18)
N1A—C6A	1.395 (2)	N1B—C6B	1.3976 (19)
N2A—C7A	1.3594 (19)	N2B—C7B	1.3608 (18)
N2A—N3A	1.3831 (17)	N2B—N3B	1.3735 (17)
N2A—H1NA	0.9319	N2B—H1NB	0.7882
N3A—C8A	1.2862 (19)	N3B—C8B	1.2906 (19)
C1A—C2A	1.387 (2)	C1B—C2B	1.394 (2)
C1A—C6A	1.411 (2)	C1B—C6B	1.403 (2)
C2A—C3A	1.383 (2)	C2B—C3B	1.379 (2)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.384 (2)	C3B—C4B	1.381 (2)
C4A—C5A	1.385 (2)	C4B—C5B	1.389 (2)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.401 (2)	C5B—C6B	1.3989 (19)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C8A—C9A	1.492 (2)	C8B—C9B	1.4831 (19)
C8A—C15A	1.502 (2)	C8B—C15B	1.507 (2)
C9A—C10A	1.395 (2)	C9B—C14B	1.396 (2)
C9A—C14A	1.400 (2)	C9B—C10B	1.399 (2)
C10A—C11A	1.395 (2)	C10B—C11B	1.391 (2)
C10A—H10B	0.9500	C10B—H10A	0.9500
C11A—C12A	1.386 (3)	C11B—C12B	1.381 (3)
C11A—H11B	0.9500	C11B—H11A	0.9500
C12A—C13A	1.390 (2)	C12B—C13B	1.397 (2)
C12A—H12B	0.9500	C12B—H12A	0.9500
C13A—C14A	1.389 (2)	C13B—C14B	1.391 (2)
C13A—H13B	0.9500	C13B—H13A	0.9500
C14A—H14B	0.9500	C14B—H14A	0.9500
C15A—H15D	0.9800	C15B—H15A	0.9800
C15A—H15E	0.9800	C15B—H15B	0.9800
C15A—H15F	0.9800	C15B—H15C	0.9800

C1A—S1A—C7A	87.80 (7)	C1B—S1B—C7B	88.19 (7)
C7A—N1A—C6A	109.10 (13)	C7B—N1B—C6B	109.69 (13)
C7A—N2A—N3A	113.78 (13)	C7B—N2B—N3B	115.76 (12)
C7A—N2A—H1NA	118.6	C7B—N2B—H1NB	117.1
N3A—N2A—H1NA	119.8	N3B—N2B—H1NB	122.8
C8A—N3A—N2A	119.03 (13)	C8B—N3B—N2B	118.47 (13)
C2A—C1A—C6A	121.90 (14)	C2B—C1B—C6B	121.68 (13)
C2A—C1A—S1A	128.01 (12)	C2B—C1B—S1B	128.46 (12)
C6A—C1A—S1A	110.08 (12)	C6B—C1B—S1B	109.84 (11)
C3A—C2A—C1A	115.95 (15)	C3B—C2B—C1B	116.47 (14)
C3A—C2A—H2AA	122.0	C3B—C2B—H2BA	121.8
C1A—C2A—H2AA	122.0	C1B—C2B—H2BA	121.8
F1A—C3A—C2A	117.48 (15)	F1B—C3B—C2B	117.68 (14)
F1A—C3A—C4A	118.20 (14)	F1B—C3B—C4B	118.38 (13)
C2A—C3A—C4A	124.32 (15)	C2B—C3B—C4B	123.93 (14)
C3A—C4A—C5A	119.11 (14)	C3B—C4B—C5B	118.94 (13)
C3A—C4A—H4AA	120.4	C3B—C4B—H4BA	120.5
C5A—C4A—H4AA	120.4	C5B—C4B—H4BA	120.5
C4A—C5A—C6A	119.00 (15)	C4B—C5B—C6B	119.48 (14)
C4A—C5A—H5AA	120.5	C4B—C5B—H5BA	120.3
C6A—C5A—H5AA	120.5	C6B—C5B—H5BA	120.3
N1A—C6A—C5A	125.09 (14)	N1B—C6B—C5B	125.34 (14)
N1A—C6A—C1A	115.19 (13)	N1B—C6B—C1B	115.16 (12)
C5A—C6A—C1A	119.71 (15)	C5B—C6B—C1B	119.49 (14)
N1A—C7A—N2A	123.27 (14)	N1B—C7B—N2B	123.47 (14)
N1A—C7A—S1A	117.84 (12)	N1B—C7B—S1B	117.10 (11)
N2A—C7A—S1A	118.87 (11)	N2B—C7B—S1B	119.42 (11)
N3A—C8A—C9A	114.63 (14)	N3B—C8B—C9B	115.75 (13)
N3A—C8A—C15A	125.59 (14)	N3B—C8B—C15B	125.78 (14)
C9A—C8A—C15A	119.75 (13)	C9B—C8B—C15B	118.47 (13)
C10A—C9A—C14A	118.33 (14)	C14B—C9B—C10B	118.65 (13)
C10A—C9A—C8A	121.20 (15)	C14B—C9B—C8B	120.69 (13)
C14A—C9A—C8A	120.36 (13)	C10B—C9B—C8B	120.65 (14)
C9A—C10A—C11A	120.53 (15)	C11B—C10B—C9B	120.98 (15)
C9A—C10A—H10B	119.7	C11B—C10B—H10A	119.5
C11A—C10A—H10B	119.7	C9B—C10B—H10A	119.5
C12A—C11A—C10A	120.59 (15)	C12B—C11B—C10B	119.90 (15)
C12A—C11A—H11B	119.7	C12B—C11B—H11A	120.0
C10A—C11A—H11B	119.7	C10B—C11B—H11A	120.0
C11A—C12A—C13A	119.33 (15)	C11B—C12B—C13B	119.84 (15)
C11A—C12A—H12B	120.3	C11B—C12B—H12A	120.1
C13A—C12A—H12B	120.3	C13B—C12B—H12A	120.1
C14A—C13A—C12A	120.21 (16)	C14B—C13B—C12B	120.24 (16)
C14A—C13A—H13B	119.9	C14B—C13B—H13A	119.9
C12A—C13A—H13B	119.9	C12B—C13B—H13A	119.9
C13A—C14A—C9A	120.99 (15)	C13B—C14B—C9B	120.37 (14)
C13A—C14A—H14B	119.5	C13B—C14B—H14A	119.8
C9A—C14A—H14B	119.5	C9B—C14B—H14A	119.8
C8A—C15A—H15D	109.5	C8B—C15B—H15A	109.5
C8A—C15A—H15E	109.5	C8B—C15B—H15B	109.5
H15D—C15A—H15E	109.5	H15A—C15B—H15B	109.5
C8A—C15A—H15F	109.5	C8B—C15B—H15C	109.5
H15D—C15A—H15F	109.5	H15A—C15B—H15C	109.5
H15E—C15A—H15F	109.5	H15B—C15B—H15C	109.5

C7A—N2A—N3A—C8A	177.41 (14)	C7B—N2B—N3B—C8B	174.69 (14)
C7A—S1A—C1A—C2A	−178.25 (16)	C7B—S1B—C1B—C2B	−177.91 (15)
C7A—S1A—C1A—C6A	0.09 (12)	C7B—S1B—C1B—C6B	0.62 (11)
C6A—C1A—C2A—C3A	0.6 (2)	C6B—C1B—C2B—C3B	0.4 (2)
S1A—C1A—C2A—C3A	178.81 (13)	S1B—C1B—C2B—C3B	178.78 (12)
C1A—C2A—C3A—F1A	−179.81 (14)	C1B—C2B—C3B—F1B	−179.57 (13)
C1A—C2A—C3A—C4A	0.0 (2)	C1B—C2B—C3B—C4B	0.6 (2)
F1A—C3A—C4A—C5A	178.95 (14)	F1B—C3B—C4B—C5B	179.14 (14)
C2A—C3A—C4A—C5A	−0.9 (3)	C2B—C3B—C4B—C5B	−1.0 (2)
C3A—C4A—C5A—C6A	1.0 (2)	C3B—C4B—C5B—C6B	0.4 (2)
C7A—N1A—C6A—C5A	178.88 (15)	C7B—N1B—C6B—C5B	178.95 (14)
C7A—N1A—C6A—C1A	0.23 (19)	C7B—N1B—C6B—C1B	−0.19 (18)
C4A—C5A—C6A—N1A	−178.99 (14)	C4B—C5B—C6B—N1B	−178.61 (14)
C4A—C5A—C6A—C1A	−0.4 (2)	C4B—C5B—C6B—C1B	0.5 (2)
C2A—C1A—C6A—N1A	178.25 (14)	C2B—C1B—C6B—N1B	178.26 (13)
S1A—C1A—C6A—N1A	−0.20 (17)	S1B—C1B—C6B—N1B	−0.39 (16)
C2A—C1A—C6A—C5A	−0.5 (2)	C2B—C1B—C6B—C5B	−0.9 (2)
S1A—C1A—C6A—C5A	−178.93 (12)	S1B—C1B—C6B—C5B	−179.59 (11)
C6A—N1A—C7A—N2A	178.47 (14)	C6B—N1B—C7B—N2B	179.28 (14)
C6A—N1A—C7A—S1A	−0.16 (17)	C6B—N1B—C7B—S1B	0.72 (16)
N3A—N2A—C7A—N1A	173.87 (14)	N3B—N2B—C7B—N1B	179.62 (14)
N3A—N2A—C7A—S1A	−7.51 (18)	N3B—N2B—C7B—S1B	−1.86 (18)
C1A—S1A—C7A—N1A	0.05 (13)	C1B—S1B—C7B—N1B	−0.81 (13)
C1A—S1A—C7A—N2A	−178.65 (13)	C1B—S1B—C7B—N2B	−179.43 (13)
N2A—N3A—C8A—C9A	175.07 (13)	N2B—N3B—C8B—C9B	−179.60 (13)
N2A—N3A—C8A—C15A	−2.9 (2)	N2B—N3B—C8B—C15B	−0.8 (2)
N3A—C8A—C9A—C10A	176.81 (14)	N3B—C8B—C9B—C14B	−16.3 (2)
C15A—C8A—C9A—C10A	−5.1 (2)	C15B—C8B—C9B—C14B	164.85 (14)
N3A—C8A—C9A—C14A	−7.2 (2)	N3B—C8B—C9B—C10B	162.52 (14)
C15A—C8A—C9A—C14A	170.95 (14)	C15B—C8B—C9B—C10B	−16.3 (2)
C14A—C9A—C10A—C11A	−0.8 (2)	C14B—C9B—C10B—C11B	1.5 (2)
C8A—C9A—C10A—C11A	175.31 (15)	C8B—C9B—C10B—C11B	−177.34 (15)
C9A—C10A—C11A—C12A	−0.6 (3)	C9B—C10B—C11B—C12B	−0.9 (2)
C10A—C11A—C12A—C13A	1.4 (3)	C10B—C11B—C12B—C13B	0.0 (3)
C11A—C12A—C13A—C14A	−0.6 (3)	C11B—C12B—C13B—C14B	0.3 (2)
C12A—C13A—C14A—C9A	−0.8 (3)	C12B—C13B—C14B—C9B	0.2 (2)
C10A—C9A—C14A—C13A	1.5 (2)	C10B—C9B—C14B—C13B	−1.1 (2)
C8A—C9A—C14A—C13A	−174.61 (15)	C8B—C9B—C14B—C13B	177.69 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1NA···N1Aⁱ	0.93	1.99	2.902 (2)	165
N2B—H1NB···N1Bⁱⁱ	0.79	2.14	2.9184 (18)	168
C5B—H5BA···F1Bⁱⁱⁱ	0.95	2.51	3.310 (2)	142
C12B—H12A···F1A^iv	0.95	2.52	3.289 (2)	138
C12A—H12B···F1B^v	0.95	2.43	3.200 (2)	138
C15B—H15A···N1Bⁱⁱ	0.98	2.57	3.503 (2)	160

Symmetry codes: (i) −x+2, y, −z+3/2; (ii) −x+1, y, −z+3/2; (iii) x, −y+2, z−1/2; (iv) −x+2, y, −z+5/2; (v) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂FN₃S
M_r	285.34
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	100
a, b, c (Å)	28.312 (3), 7.2952 (7), 13.0626 (13)
β (°)	103.151 (2)
V (Å³)	2627.2 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.46 × 0.21 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.894, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	52781, 7411, 7049
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.697

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.080, 1.06
No. of reflections	7411
No. of parameters	364
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.43

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1NA···N1Aⁱ	0.93	1.99	2.902 (2)	165
N2B—H1NB···N1Bⁱⁱ	0.79	2.14	2.9184 (18)	168
C5B—H5BA···F1Bⁱⁱⁱ	0.95	2.51	3.310 (2)	142
C12B—H12A···F1A^iv	0.95	2.52	3.289 (2)	138
C12A—H12B···F1B^v	0.95	2.43	3.200 (2)	138
C15B—H15A···N1Bⁱⁱ	0.98	2.57	3.503 (2)	160

Symmetry codes: (i) −x+2, y, −z+3/2; (ii) −x+1, y, −z+3/2; (iii) x, −y+2, z−1/2; (iv) −x+2, y, −z+5/2; (v) −x+1, −y+2, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors would like to thank Universiti Sains Malaysia (USM) for the Research University Grant No. 1001/PFIZIK/811160. MH and DM gratefully acknowledge the School of Advanced Sciences, VIT, Vellore, for providing research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Al-Soud, Y. A., Al-Sa'doni, H., Amajaour, H. A. S. & Al-Masoudi, N. A. (2006). Z. Naturforsch. Teil B, 62, 523–528. Google Scholar
Bowyer, P. W., Gunaratne, R. S., Grainger, M., Withers-Martinez, C., Wickramsinghe, S. R., Tate, E. W., Leatherbarrow, R. J., Brown, K. A., Holder, A. A. & Smith, D. F. (2007). Biochem. J. 408, 173–180. Web of Science PubMed CAS Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gurupadayya, B. M., Gopal, M., Padmashali, B. & Manohara, Y. N. (2008). Indian J. Pharm. Sci. 70, 572–577. Web of Science CAS PubMed Google Scholar
Kini, S., Swain, S. P. & Gandhi, A. M. (2007). Indian J. Pharm. Sci. 69, 46–50. CrossRef CAS Google Scholar
Mittal, S., Samottra, M. K., Kaur, J. & Gita, S. (2007). Phosphorus Sulfur Silicon Relat. Elem. 182, 2105–2113. Web of Science CrossRef CAS Google Scholar
Munirajasekhar, D., Himaja, M. & Sunil, V. M. (2011). Int. Res. J. Pharm. 2, 114–117. CAS Google Scholar
Pozas, R., Carballo, J., Castro, C. & Rubio, J. (2005). Bioorg. Med. Chem. Lett. 15, 1417–1421. Web of Science CrossRef PubMed CAS Google Scholar
Rana, A., Siddiqui, N. & Khan, S. (2008). Eur. J. Med. Chem. 43, 1114–1122. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar