6-Fluoro-2-(4-meth­oxy­phen­yl)imidazo[2,1-b][1,3]benzothia­zole

Fun, H.-K.; Hemamalini, M.; Umesha, K.; Sarojini, B.K.; Narayana, B.

doi:10.1107/S1600536811046666

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages o3265-o3266

https://doi.org/10.1107/S1600536811046666

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6-Fluoro-2-(4-methoxyphenyl)imidazo[2,1-b][1,3]benzothiazole

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a K. Umesha,^b B. K. Sarojini ^b and B. Narayana ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India, and ^cDepartment of Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 3 November 2011; accepted 5 November 2011; online 12 November 2011)

The asymmetric unit of the title compound, C₁₆H₁₁FN₂OS, comprises two independent molecules in which the benzothiazole rings are essentially planar, with maximum deviations of 0.038 (2) and 0.045 (3) Å. The central benzothiazole ring makes dihedral angles of 4.87 (13) and 0.64 (12)° and 4.04 (12) and 3.67 (12)° with the two terminal phenyl rings in the two independent molecules. In the crystal, molecules are connected via weak intermolecular C—H⋯O hydrogen bonds forming supramolecular chains along the c axis.

Related literature

For details and applications of benzothiazoles, see: Yaseen et al. (2006 ); Kini et al. (2007 ); Munirajasekhar et al. (2011 ); Gurupadayya et al. (2008 ); Mittal et al. (2007 ); Bowyer et al. (2007 ); Pozas et al. (2005 ); Rana et al. (2008 ); Saha et al. (2000 ); Katritzky & Rees (1984 ). For bond-length data, see: Allen et al. (1987 ). For a related structure, see: Fun et al. (2011 ).

Experimental

Crystal data

C₁₆H₁₁FN₂OS
M_r = 298.33
Monoclinic, P 2₁
a = 7.6120 (13) Å
b = 13.883 (2) Å
c = 13.049 (2) Å
β = 105.117 (3)°
V = 1331.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.31 × 0.30 × 0.13 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.926, T_max = 0.967
20506 measured reflections
7656 independent reflections
4268 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.116
S = 1.00
7656 reflections
381 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 3649 Friedel pairs
Flack parameter: 0.00 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6A—H6AA⋯O1Aⁱ	0.93	2.53	3.367 (5)	149
C6B—H6BA⋯O1Bⁱ	0.93	2.52	3.382 (4)	153
Symmetry code: (i) x+1, y, z+1.

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/S1600536811046666/bq2315sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046666/bq2315Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811046666/bq2315Isup3.cml

checkCIF report

Comment top

Benzothiazoles are very important bicyclic ring 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. Literature review has shown that benzothiazoles and their derivatives show considerable properties, including potent inhibition of human immunodeficiency virus type 1 (HIV-1), replication by HIV-1 protease (Yaseen 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 (Pozas et al., 2005) and various CNS activities (Rana et al., 2008). Imidazole has become an important part of many pharmaceuticals. Synthetic imidazoles are present in many fungicides and antifungals (Saha et al., 2000), antiprotozoal and antihypertensive medications. Imidazole is part of the theophylline molecule, found in tea leaves and coffee beans, that stimulates the central nervous system. It is present in the anticancer medication mercaptopurine, which combats leukemia by interfering with DNA activities (Katritzky & Rees, 1984). The structure of a related compound 7-Chloro-3-phenylbenzo[4,5]thiazolo-[2,3-c][1,2,4] triazole has been reported by Fun et al., 2011.

In continuation of our research investigation, a new fused imidazo[2,1-b]thiazole derivative was prepared by the reaction of flurobenzothiazole amine with 4-methoxy phenacyl bromide under microwave irradiation at 130 °C and its crystal structure is reported here.

The asymmetric unit of the title compound consists of two crystallographically independent molecules, (A & B), as shown in Fig. 1. The bond lengths and angles of molecules A and B agree with each other and are within normal ranges (Allen et al., 1987). The benzothiazole units are essentially planar with maximum deviations of 0.038 (2) Å for atom N1A (molecule A) and 0.045 (3) Å for atom C7B (molecule B). The dihedral angles that the central benzothiazole (S1/N1,N2/C1,C2,C7–C9) ring makes with the two terminal phenyl (C2–C7/C10–C15) rings in the two independent molecules are 4.87 (13)° : 0.64 (12)° for molecule A and 4.04 (12)° : 3.67 (12)° for molecule B.

In the crystal structure (Fig. 2), the molecules are connected via weak intermolecular C—H···O hydrogen bonds forming one-dimensional supramolecular chains along the c-axis.

Related literature top

For details and applications of benzothiazoles, see: Yaseen et al. (2006); Kini et al. (2007); Munirajasekhar et al. (2011); Gurupadayya et al. (2008); Mittal et al. (2007); Bowyer et al. (2007); Pozas et al. (2005); Rana et al. (2008); Saha et al. (2000); Katritzky & Rees (1984). For bond-length data, see: Allen et al. (1987). For a related structure, see: Fun et al. (2011).

Experimental top

A mixture of 5-fluorobenzothiazole amine (0.5 g, 2.99 mmol) and 2-bromo-1- (4-methoxyphenyl)ethanone (0.75 g, 3.29 mmol) in ethanol (10 ml) were irradiated with microwave at 130 °C for 45 min. The solvent was evaporated under reduced pressure and the residue was dissolved in dichloromethane (50 ml), washed with 10% sodium bicarbonate (2 X 50 ml), water (50 ml) and finally with saturated brine solution (2 X 50 ml). The organic layer was dried using anhydrous sodium sulphate and then evaporated under vacuum. The crude material was recrystallized by using dichloromethane and methanol to afford the title compound (0.7 g, 78 %) as colorless crystals. mp:450.9–451.9 K (Solvent of Crystallization: 1:1 dichloromethane : methanol).

Structure description top

In the crystal structure (Fig. 2), the molecules are connected via weak intermolecular C—H···O hydrogen bonds forming one-dimensional supramolecular chains along the c-axis.

For details and applications of benzothiazoles, see: Yaseen et al. (2006); Kini et al. (2007); Munirajasekhar et al. (2011); Gurupadayya et al. (2008); Mittal et al. (2007); Bowyer et al. (2007); Pozas et al. (2005); Rana et al. (2008); Saha et al. (2000); Katritzky & Rees (1984). For bond-length data, see: Allen et al. (1987). For a related structure, see: Fun et al. (2011).

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. An ORTEP view of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound (I). H atoms are not involing the hydrogen bond interactions are omitted for clarity.

6-Fluoro-2-(4-methoxyphenyl)imidazo[2,1-b][1,3]benzothiazole top

Crystal data top

C₁₆H₁₁FN₂OS	F(000) = 616
M_r = 298.33	D_x = 1.488 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3518 reflections
a = 7.6120 (13) Å	θ = 2.2–23.5°
b = 13.883 (2) Å	µ = 0.25 mm⁻¹
c = 13.049 (2) Å	T = 296 K
β = 105.117 (3)°	Block, colourless
V = 1331.3 (4) Å³	0.31 × 0.30 × 0.13 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	7656 independent reflections
Radiation source: fine-focus sealed tube	4268 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
φ and ω scans	θ_max = 30.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→10
T_min = 0.926, T_max = 0.967	k = −19→19
20506 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0433P)² + 0.0628P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
7656 reflections	Δρ_max = 0.24 e Å⁻³
381 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3649 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (8)

Crystal data top

C₁₆H₁₁FN₂OS	V = 1331.3 (4) Å³
M_r = 298.33	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 7.6120 (13) Å	µ = 0.25 mm⁻¹
b = 13.883 (2) Å	T = 296 K
c = 13.049 (2) Å	0.31 × 0.30 × 0.13 mm
β = 105.117 (3)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	7656 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4268 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.967	R_int = 0.051
20506 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.116	Δρ_max = 0.24 e Å⁻³
S = 1.00	Δρ_min = −0.25 e Å⁻³
7656 reflections	Absolute structure: Flack (1983), 3649 Friedel pairs
381 parameters	Absolute structure parameter: 0.00 (8)
1 restraint

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	0.85944 (11)	1.02159 (6)	0.83180 (6)	0.0574 (2)
F1A	1.5287 (3)	0.92386 (17)	0.98451 (18)	0.0787 (7)
O1A	0.1100 (4)	0.95521 (17)	0.15032 (18)	0.0642 (7)
N1A	0.9233 (4)	0.96545 (17)	0.65606 (19)	0.0406 (6)
N2A	0.6279 (4)	1.00305 (19)	0.62596 (19)	0.0499 (7)
C1A	0.8431 (5)	0.9457 (2)	0.5494 (2)	0.0447 (8)
H1AA	0.8999	0.9213	0.4999	0.054*
C2A	1.0919 (5)	0.9560 (2)	0.7307 (3)	0.0416 (8)
C3A	1.2520 (5)	0.9211 (2)	0.7145 (3)	0.0462 (8)
H3AA	1.2599	0.9045	0.6468	0.055*
C4A	1.4000 (5)	0.9111 (2)	0.8010 (3)	0.0517 (9)
H4AA	1.5099	0.8876	0.7927	0.062*
C5A	1.3830 (5)	0.9365 (2)	0.9004 (3)	0.0529 (9)
C6A	1.2256 (5)	0.9728 (3)	0.9189 (3)	0.0513 (9)
H6AA	1.2195	0.9902	0.9867	0.062*
C7A	1.0774 (5)	0.9822 (2)	0.8322 (2)	0.0448 (7)
C8A	0.7857 (5)	0.9987 (2)	0.6965 (3)	0.0475 (8)
C9A	0.6656 (5)	0.9695 (2)	0.5327 (3)	0.0442 (8)
C10A	0.5183 (4)	0.9645 (2)	0.4339 (2)	0.0419 (7)
C11A	0.5515 (5)	0.9338 (2)	0.3389 (3)	0.0512 (9)
H11A	0.6680	0.9147	0.3376	0.061*
C12A	0.4119 (5)	0.9315 (2)	0.2468 (3)	0.0535 (9)
H12A	0.4354	0.9107	0.1840	0.064*
C13A	0.2379 (5)	0.9599 (2)	0.2466 (2)	0.0469 (8)
C14A	0.2027 (5)	0.9902 (2)	0.3400 (2)	0.0489 (8)
H14A	0.0862	1.0094	0.3410	0.059*
C15A	0.3434 (5)	0.9915 (2)	0.4323 (2)	0.0485 (8)
H15A	0.3189	1.0113	0.4952	0.058*
C16A	−0.0712 (5)	0.9810 (3)	0.1471 (3)	0.0736 (11)
H16A	−0.1439	0.9797	0.0749	0.110*
H16B	−0.0730	1.0446	0.1755	0.110*
H16C	−0.1196	0.9361	0.1886	0.110*
S1B	0.44615 (11)	0.65085 (6)	0.87504 (6)	0.0551 (2)
F1B	1.1185 (3)	0.74352 (15)	1.02571 (15)	0.0727 (6)
O1B	−0.3004 (4)	0.72079 (18)	0.19408 (19)	0.0642 (7)
N1B	0.5109 (4)	0.70099 (17)	0.6977 (2)	0.0420 (7)
N2B	0.2174 (4)	0.6637 (2)	0.6678 (2)	0.0471 (7)
C1B	0.4345 (5)	0.7183 (2)	0.5919 (2)	0.0449 (8)
H1BA	0.4932	0.7411	0.5425	0.054*
C2B	0.6794 (4)	0.71310 (19)	0.7725 (2)	0.0379 (7)
C3B	0.8426 (5)	0.7428 (2)	0.7558 (3)	0.0450 (8)
H3BA	0.8528	0.7565	0.6878	0.054*
C4B	0.9899 (5)	0.7517 (2)	0.8425 (3)	0.0496 (8)
H4BA	1.1021	0.7708	0.8336	0.060*
C5B	0.9712 (5)	0.7326 (2)	0.9415 (3)	0.0500 (9)
C6B	0.8146 (5)	0.7013 (2)	0.9615 (2)	0.0496 (8)
H6BA	0.8072	0.6879	1.0301	0.060*
C7B	0.6651 (4)	0.6903 (2)	0.8739 (2)	0.0427 (8)
C8B	0.3730 (4)	0.6691 (2)	0.7379 (2)	0.0444 (7)
C9B	0.2543 (5)	0.6953 (2)	0.5740 (2)	0.0417 (8)
C10B	0.1091 (5)	0.7020 (2)	0.4758 (3)	0.0423 (8)
C11B	0.1394 (5)	0.7359 (2)	0.3813 (2)	0.0506 (8)
H11B	0.2560	0.7550	0.3802	0.061*
C12B	0.0013 (5)	0.7417 (3)	0.2897 (3)	0.0554 (9)
H12B	0.0248	0.7652	0.2279	0.066*
C13B	−0.1737 (5)	0.7124 (2)	0.2892 (2)	0.0472 (8)
C14B	−0.2083 (5)	0.6788 (2)	0.3807 (3)	0.0505 (9)
H14B	−0.3251	0.6595	0.3811	0.061*
C15B	−0.0671 (5)	0.6739 (2)	0.4732 (2)	0.0489 (8)
H15B	−0.0915	0.6512	0.5351	0.059*
C16B	−0.4794 (5)	0.6850 (3)	0.1868 (3)	0.0671 (10)
H16D	−0.5526	0.6914	0.1151	0.101*
H16E	−0.5333	0.7213	0.2334	0.101*
H16F	−0.4724	0.6184	0.2071	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.0490 (6)	0.0787 (6)	0.0442 (5)	0.0094 (4)	0.0113 (4)	−0.0105 (4)
F1A	0.0579 (17)	0.1000 (16)	0.0651 (15)	0.0116 (13)	−0.0074 (12)	−0.0116 (12)
O1A	0.0589 (18)	0.0840 (17)	0.0428 (13)	0.0008 (14)	0.0007 (12)	−0.0052 (12)
N1A	0.0385 (18)	0.0436 (14)	0.0396 (15)	0.0029 (12)	0.0104 (12)	0.0004 (12)
N2A	0.0422 (17)	0.0633 (18)	0.0431 (14)	0.0056 (14)	0.0093 (12)	−0.0042 (12)
C1A	0.053 (2)	0.0441 (17)	0.0376 (17)	−0.0003 (14)	0.0128 (15)	0.0002 (12)
C2A	0.045 (2)	0.0360 (16)	0.0452 (18)	0.0008 (15)	0.0144 (15)	0.0016 (13)
C3A	0.050 (2)	0.0409 (16)	0.0503 (19)	0.0022 (15)	0.0175 (17)	−0.0004 (14)
C4A	0.041 (2)	0.0457 (18)	0.068 (3)	0.0004 (16)	0.0143 (19)	−0.0006 (16)
C5A	0.047 (2)	0.053 (2)	0.053 (2)	−0.0049 (16)	0.0036 (17)	−0.0041 (15)
C6A	0.052 (2)	0.055 (2)	0.0446 (19)	−0.0062 (17)	0.0102 (16)	−0.0063 (16)
C7A	0.049 (2)	0.0423 (16)	0.0439 (18)	−0.0001 (15)	0.0130 (15)	−0.0045 (14)
C8A	0.043 (2)	0.054 (2)	0.0478 (19)	0.0048 (16)	0.0155 (15)	−0.0044 (15)
C9A	0.047 (2)	0.0408 (16)	0.0464 (19)	−0.0011 (15)	0.0158 (17)	0.0000 (14)
C10A	0.046 (2)	0.0383 (15)	0.0397 (17)	−0.0018 (14)	0.0077 (14)	0.0010 (13)
C11A	0.050 (2)	0.056 (2)	0.048 (2)	0.0050 (16)	0.0141 (17)	0.0003 (16)
C12A	0.058 (3)	0.064 (2)	0.0387 (18)	0.0004 (17)	0.0125 (17)	−0.0032 (15)
C13A	0.049 (2)	0.0462 (16)	0.0408 (18)	−0.0026 (16)	0.0035 (16)	0.0037 (14)
C14A	0.045 (2)	0.0543 (19)	0.0470 (18)	0.0061 (15)	0.0106 (15)	−0.0025 (14)
C15A	0.052 (2)	0.0525 (19)	0.0405 (18)	−0.0007 (15)	0.0112 (16)	−0.0036 (14)
C16A	0.052 (3)	0.094 (3)	0.064 (2)	0.005 (2)	−0.0045 (18)	0.001 (2)
S1B	0.0432 (5)	0.0785 (6)	0.0425 (4)	−0.0067 (4)	0.0093 (4)	0.0115 (4)
F1B	0.0498 (13)	0.0932 (14)	0.0636 (13)	−0.0094 (11)	−0.0058 (10)	0.0097 (12)
O1B	0.0554 (18)	0.0845 (18)	0.0456 (13)	−0.0021 (14)	0.0009 (12)	0.0108 (13)
N1B	0.0400 (18)	0.0464 (15)	0.0398 (15)	−0.0022 (12)	0.0106 (13)	−0.0020 (12)
N2B	0.0417 (17)	0.0549 (16)	0.0433 (14)	−0.0053 (14)	0.0085 (12)	0.0012 (13)
C1B	0.051 (2)	0.0484 (18)	0.0355 (16)	−0.0038 (15)	0.0121 (15)	0.0004 (13)
C2B	0.0339 (19)	0.0384 (15)	0.0403 (16)	0.0028 (13)	0.0077 (13)	−0.0004 (12)
C3B	0.044 (2)	0.0478 (17)	0.0433 (18)	0.0049 (15)	0.0117 (16)	0.0020 (15)
C4B	0.045 (2)	0.0444 (17)	0.062 (2)	−0.0003 (14)	0.0171 (17)	0.0073 (15)
C5B	0.041 (2)	0.0504 (18)	0.051 (2)	0.0024 (16)	−0.0016 (16)	0.0024 (16)
C6B	0.047 (2)	0.0557 (18)	0.0439 (17)	0.0006 (15)	0.0078 (15)	0.0057 (14)
C7B	0.038 (2)	0.0452 (17)	0.0450 (18)	0.0004 (14)	0.0106 (15)	0.0011 (14)
C8B	0.045 (2)	0.0483 (17)	0.0424 (17)	−0.0028 (15)	0.0157 (15)	0.0026 (14)
C9B	0.045 (2)	0.0432 (16)	0.0373 (17)	−0.0023 (14)	0.0109 (15)	−0.0033 (13)
C10B	0.044 (2)	0.0404 (16)	0.0413 (17)	−0.0024 (14)	0.0083 (15)	−0.0021 (13)
C11B	0.046 (2)	0.0609 (19)	0.0445 (18)	−0.0049 (16)	0.0112 (16)	0.0048 (16)
C12B	0.059 (3)	0.065 (2)	0.0424 (19)	−0.0071 (19)	0.0131 (17)	0.0091 (18)
C13B	0.052 (2)	0.0453 (17)	0.0399 (17)	0.0036 (15)	0.0037 (15)	0.0005 (13)
C14B	0.041 (2)	0.061 (2)	0.049 (2)	−0.0031 (16)	0.0096 (16)	−0.0005 (16)
C15B	0.051 (2)	0.0530 (18)	0.0424 (17)	−0.0059 (15)	0.0106 (15)	0.0026 (14)
C16B	0.048 (2)	0.081 (3)	0.060 (2)	0.0003 (19)	−0.0078 (17)	−0.0053 (18)

Geometric parameters (Å, º) top

S1A—C8A	1.737 (4)	S1B—C8B	1.748 (3)
S1A—C7A	1.746 (3)	S1B—C7B	1.758 (3)
F1A—C5A	1.353 (4)	F1B—C5B	1.359 (3)
O1A—C13A	1.376 (4)	O1B—C13B	1.364 (3)
O1A—C16A	1.415 (4)	O1B—C16B	1.430 (4)
N1A—C8A	1.369 (4)	N1B—C8B	1.364 (4)
N1A—C1A	1.394 (4)	N1B—C1B	1.373 (4)
N1A—C2A	1.400 (4)	N1B—C2B	1.405 (3)
N2A—C8A	1.311 (4)	N2B—C8B	1.296 (4)
N2A—C9A	1.401 (4)	N2B—C9B	1.396 (4)
C1A—C9A	1.352 (5)	C1B—C9B	1.368 (4)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.378 (5)	C2B—C3B	1.379 (4)
C2A—C7A	1.405 (4)	C2B—C7B	1.392 (4)
C3A—C4A	1.379 (4)	C3B—C4B	1.375 (4)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.382 (5)	C4B—C5B	1.362 (5)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.378 (5)	C5B—C6B	1.357 (5)
C6A—C7A	1.380 (4)	C6B—C7B	1.396 (4)
C6A—H6AA	0.9300	C6B—H6BA	0.9300
C9A—C10A	1.473 (4)	C9B—C10B	1.461 (4)
C10A—C15A	1.378 (4)	C10B—C15B	1.389 (5)
C10A—C11A	1.394 (4)	C10B—C11B	1.394 (4)
C11A—C12A	1.382 (4)	C11B—C12B	1.372 (4)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.381 (5)	C12B—C13B	1.391 (5)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.379 (4)	C13B—C14B	1.370 (4)
C14A—C15A	1.388 (4)	C14B—C15B	1.393 (4)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—H16A	0.9600	C16B—H16D	0.9600
C16A—H16B	0.9600	C16B—H16E	0.9600
C16A—H16C	0.9600	C16B—H16F	0.9600

C8A—S1A—C7A	90.01 (16)	C8B—S1B—C7B	89.75 (16)
C13A—O1A—C16A	117.9 (3)	C13B—O1B—C16B	117.8 (3)
C8A—N1A—C1A	105.7 (3)	C8B—N1B—C1B	106.1 (3)
C8A—N1A—C2A	114.7 (3)	C8B—N1B—C2B	115.2 (2)
C1A—N1A—C2A	139.4 (3)	C1B—N1B—C2B	138.4 (3)
C8A—N2A—C9A	103.7 (3)	C8B—N2B—C9B	104.2 (3)
C9A—C1A—N1A	105.8 (3)	C9B—C1B—N1B	105.9 (3)
C9A—C1A—H1AA	127.1	C9B—C1B—H1BA	127.1
N1A—C1A—H1AA	127.1	N1B—C1B—H1BA	127.1
C3A—C2A—N1A	127.8 (3)	C3B—C2B—C7B	121.0 (3)
C3A—C2A—C7A	121.7 (3)	C3B—C2B—N1B	128.5 (3)
N1A—C2A—C7A	110.4 (3)	C7B—C2B—N1B	110.4 (3)
C2A—C3A—C4A	118.5 (3)	C4B—C3B—C2B	118.1 (3)
C2A—C3A—H3AA	120.8	C4B—C3B—H3BA	120.9
C4A—C3A—H3AA	120.8	C2B—C3B—H3BA	120.9
C3A—C4A—C5A	119.1 (3)	C5B—C4B—C3B	119.9 (3)
C3A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.1
C5A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.1
F1A—C5A—C6A	118.2 (3)	C6B—C5B—F1B	117.5 (3)
F1A—C5A—C4A	118.0 (3)	C6B—C5B—C4B	124.0 (3)
C6A—C5A—C4A	123.8 (3)	F1B—C5B—C4B	118.5 (3)
C5A—C6A—C7A	117.0 (3)	C5B—C6B—C7B	116.5 (3)
C5A—C6A—H6AA	121.5	C5B—C6B—H6BA	121.7
C7A—C6A—H6AA	121.5	C7B—C6B—H6BA	121.7
C6A—C7A—C2A	120.0 (3)	C2B—C7B—C6B	120.3 (3)
C6A—C7A—S1A	127.2 (2)	C2B—C7B—S1B	112.9 (2)
C2A—C7A—S1A	112.7 (2)	C6B—C7B—S1B	126.8 (2)
N2A—C8A—N1A	113.5 (3)	N2B—C8B—N1B	113.6 (3)
N2A—C8A—S1A	134.4 (2)	N2B—C8B—S1B	134.6 (2)
N1A—C8A—S1A	112.1 (3)	N1B—C8B—S1B	111.7 (2)
C1A—C9A—N2A	111.3 (3)	C1B—C9B—N2B	110.2 (3)
C1A—C9A—C10A	129.0 (3)	C1B—C9B—C10B	129.1 (3)
N2A—C9A—C10A	119.6 (3)	N2B—C9B—C10B	120.7 (3)
C15A—C10A—C11A	117.9 (3)	C15B—C10B—C11B	117.1 (3)
C15A—C10A—C9A	120.8 (3)	C15B—C10B—C9B	120.5 (3)
C11A—C10A—C9A	121.3 (3)	C11B—C10B—C9B	122.4 (3)
C12A—C11A—C10A	120.2 (3)	C12B—C11B—C10B	121.6 (3)
C12A—C11A—H11A	119.9	C12B—C11B—H11B	119.2
C10A—C11A—H11A	119.9	C10B—C11B—H11B	119.2
C13A—C12A—C11A	121.0 (3)	C11B—C12B—C13B	120.2 (3)
C13A—C12A—H12A	119.5	C11B—C12B—H12B	119.9
C11A—C12A—H12A	119.5	C13B—C12B—H12B	119.9
O1A—C13A—C14A	124.5 (3)	O1B—C13B—C14B	124.8 (3)
O1A—C13A—C12A	116.0 (3)	O1B—C13B—C12B	115.4 (3)
C14A—C13A—C12A	119.5 (3)	C14B—C13B—C12B	119.8 (3)
C13A—C14A—C15A	119.1 (3)	C13B—C14B—C15B	119.4 (3)
C13A—C14A—H14A	120.4	C13B—C14B—H14B	120.3
C15A—C14A—H14A	120.4	C15B—C14B—H14B	120.3
C10A—C15A—C14A	122.2 (3)	C10B—C15B—C14B	122.0 (3)
C10A—C15A—H15A	118.9	C10B—C15B—H15B	119.0
C14A—C15A—H15A	118.9	C14B—C15B—H15B	119.0
O1A—C16A—H16A	109.5	O1B—C16B—H16D	109.5
O1A—C16A—H16B	109.5	O1B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
O1A—C16A—H16C	109.5	O1B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5

C8A—N1A—C1A—C9A	0.9 (3)	C8B—N1B—C1B—C9B	−0.4 (3)
C2A—N1A—C1A—C9A	176.0 (3)	C2B—N1B—C1B—C9B	−174.7 (3)
C8A—N1A—C2A—C3A	177.2 (3)	C8B—N1B—C2B—C3B	179.1 (3)
C1A—N1A—C2A—C3A	2.4 (5)	C1B—N1B—C2B—C3B	−6.9 (5)
C8A—N1A—C2A—C7A	1.0 (3)	C8B—N1B—C2B—C7B	−0.9 (3)
C1A—N1A—C2A—C7A	−173.8 (3)	C1B—N1B—C2B—C7B	173.1 (3)
N1A—C2A—C3A—C4A	−175.2 (3)	C7B—C2B—C3B—C4B	−1.6 (4)
C7A—C2A—C3A—C4A	0.6 (4)	N1B—C2B—C3B—C4B	178.4 (3)
C2A—C3A—C4A—C5A	−0.1 (4)	C2B—C3B—C4B—C5B	−0.9 (4)
C3A—C4A—C5A—F1A	178.4 (3)	C3B—C4B—C5B—C6B	2.3 (5)
C3A—C4A—C5A—C6A	−0.8 (5)	C3B—C4B—C5B—F1B	−179.0 (3)
F1A—C5A—C6A—C7A	−178.1 (3)	F1B—C5B—C6B—C7B	−179.8 (3)
C4A—C5A—C6A—C7A	1.1 (5)	C4B—C5B—C6B—C7B	−1.1 (5)
C5A—C6A—C7A—C2A	−0.6 (4)	C3B—C2B—C7B—C6B	2.8 (4)
C5A—C6A—C7A—S1A	177.5 (3)	N1B—C2B—C7B—C6B	−177.2 (2)
C3A—C2A—C7A—C6A	−0.3 (4)	C3B—C2B—C7B—S1B	−178.2 (2)
N1A—C2A—C7A—C6A	176.2 (3)	N1B—C2B—C7B—S1B	1.8 (3)
C3A—C2A—C7A—S1A	−178.6 (2)	C5B—C6B—C7B—C2B	−1.4 (4)
N1A—C2A—C7A—S1A	−2.1 (3)	C5B—C6B—C7B—S1B	179.7 (3)
C8A—S1A—C7A—C6A	−176.1 (3)	C8B—S1B—C7B—C2B	−1.7 (2)
C8A—S1A—C7A—C2A	2.1 (2)	C8B—S1B—C7B—C6B	177.1 (3)
C9A—N2A—C8A—N1A	0.4 (3)	C9B—N2B—C8B—N1B	−0.7 (3)
C9A—N2A—C8A—S1A	−176.8 (3)	C9B—N2B—C8B—S1B	175.4 (3)
C1A—N1A—C8A—N2A	−0.8 (3)	C1B—N1B—C8B—N2B	0.7 (3)
C2A—N1A—C8A—N2A	−177.3 (2)	C2B—N1B—C8B—N2B	176.5 (2)
C1A—N1A—C8A—S1A	177.0 (2)	C1B—N1B—C8B—S1B	−176.3 (2)
C2A—N1A—C8A—S1A	0.5 (3)	C2B—N1B—C8B—S1B	−0.4 (3)
C7A—S1A—C8A—N2A	175.8 (3)	C7B—S1B—C8B—N2B	−174.9 (3)
C7A—S1A—C8A—N1A	−1.4 (2)	C7B—S1B—C8B—N1B	1.2 (2)
N1A—C1A—C9A—N2A	−0.7 (3)	N1B—C1B—C9B—N2B	0.0 (3)
N1A—C1A—C9A—C10A	179.1 (3)	N1B—C1B—C9B—C10B	178.6 (3)
C8A—N2A—C9A—C1A	0.2 (3)	C8B—N2B—C9B—C1B	0.4 (3)
C8A—N2A—C9A—C10A	−179.6 (3)	C8B—N2B—C9B—C10B	−178.3 (2)
C1A—C9A—C10A—C15A	179.6 (3)	C1B—C9B—C10B—C15B	179.4 (3)
N2A—C9A—C10A—C15A	−0.6 (4)	N2B—C9B—C10B—C15B	−2.2 (4)
C1A—C9A—C10A—C11A	−1.4 (5)	C1B—C9B—C10B—C11B	−0.4 (5)
N2A—C9A—C10A—C11A	178.4 (3)	N2B—C9B—C10B—C11B	178.1 (3)
C15A—C10A—C11A—C12A	0.4 (4)	C15B—C10B—C11B—C12B	0.3 (5)
C9A—C10A—C11A—C12A	−178.7 (3)	C9B—C10B—C11B—C12B	180.0 (3)
C10A—C11A—C12A—C13A	0.3 (5)	C10B—C11B—C12B—C13B	−0.7 (5)
C16A—O1A—C13A—C14A	−1.6 (5)	C16B—O1B—C13B—C14B	−5.1 (4)
C16A—O1A—C13A—C12A	178.3 (3)	C16B—O1B—C13B—C12B	175.4 (3)
C11A—C12A—C13A—O1A	179.6 (3)	C11B—C12B—C13B—O1B	−179.7 (3)
C11A—C12A—C13A—C14A	−0.5 (5)	C11B—C12B—C13B—C14B	0.7 (5)
O1A—C13A—C14A—C15A	179.9 (3)	O1B—C13B—C14B—C15B	−179.8 (3)
C12A—C13A—C14A—C15A	0.0 (5)	C12B—C13B—C14B—C15B	−0.3 (5)
C11A—C10A—C15A—C14A	−0.9 (4)	C11B—C10B—C15B—C14B	0.2 (4)
C9A—C10A—C15A—C14A	178.2 (3)	C9B—C10B—C15B—C14B	−179.6 (3)
C13A—C14A—C15A—C10A	0.7 (4)	C13B—C14B—C15B—C10B	−0.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6A—H6AA···O1Aⁱ	0.93	2.53	3.367 (5)	149
C6B—H6BA···O1Bⁱ	0.93	2.52	3.382 (4)	153

Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁FN₂OS
M_r	298.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	7.6120 (13), 13.883 (2), 13.049 (2)
β (°)	105.117 (3)
V (Å³)	1331.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.31 × 0.30 × 0.13

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.926, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	20506, 7656, 4268
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.116, 1.00
No. of reflections	7656
No. of parameters	381
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25
Absolute structure	Flack (1983), 3649 Friedel pairs
Absolute structure parameter	0.00 (8)

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
C6A—H6AA···O1Aⁱ	0.9300	2.5300	3.367 (5)	149.00
C6B—H6BA···O1Bⁱ	0.9300	2.5200	3.382 (4)	153.00

Symmetry code: (i) x+1, y, z+1.

Footnotes

‡Thomson Reuters Researcher ID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. KU and BKS gratefully acknowledge P. A. College of Engineering, Mangalore, for providing facilities to carry out the research work.

References

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