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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1-(6-Fluoro-1,3-benzo­thia­zol-2-yl)-3-phenyl-1H-pyrazole-4-carbaldehyde

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

(Received 15 November 2011; accepted 21 November 2011; online 30 November 2011)

The asymmetric unit of the title compound, C17H10FN3OS, consists of two crystallographically independent mol­ecules. In one mol­ecule, the pyrazole ring makes dihedral angles of 6.51 (7) and 34.02 (9)°, respectively, with the terminal 1,3-benzothia­zole ring system and the phenyl ring, while in the other mol­ecule these values are 6.41 (8) and 23.06 (9)°. In the crystal, the molecules are linked by weak ππ [centroid–centroid distance = 3.7069 (10) Å] and C—H⋯π inter­actions.

Related literature

For the biological activity of benzothia­zole derivatives, see: Al-Soud et al. (2006[Al-Soud, Y. A., Al-Sa'doni, H., Amajaour, H. A. S. & Al-Masoudi, A. (2006). Z. Naturforsch. Teil A, 62, 523-528.]); Kini et al. (2007[Kini, S., Swain, S. P. & Gandhi, A. M. (2007). Indian J. Pharm. Sci. 69, 46-50.]); Munirajasekhar et al. (2011[Munirajasekhar, D., Himaja, M. & Sunil, V. M. (2011). Int. Res. J. Pharm. 2, 114-117.]); Gurupadayya et al. (2008[Gurupadayya, B. M., Gopal, M., Padmashali, B. & Manohara, Y. N. (2008). Indian J. Pharm. Sci. 70, 572-577.]); Bowyer et al. (2007[Bowyer, P. W., Gunaratne, R. S., Grainge, 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.]); Mittal et al. (2007[Mittal, S., Samottra, M. K., Kaur, J. & Gita, S. (2007). Phosphorus Sulfur Silicon Relat. Elem. 9, 2105-2113.]); Rocío Pozas et al. (2005[Pozas, R., Carballo, J., Castro, C. & Rubio, J. (2005). Bioorg. Med. Chem. Lett. 15, 1417-1421.]); Rana et al. (2008[Rana, A., Siddiqui, N. & Khan, S. (2008). Eur. J. Med. Chem. 43, 1114-1122.]). For a related structure, see: Fun et al. (2011[Fun, H.-K., Arshad, S., Himaja, M., Munirajasekhar, D. & Sarojini, B. K. (2011). Acta Cryst. E67, o2412.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C17H10FN3OS

  • Mr = 323.34

  • Triclinic, [P \overline 1]

  • a = 8.0994 (3) Å

  • b = 13.6566 (4) Å

  • c = 13.8472 (5) Å

  • α = 70.393 (1)°

  • β = 85.264 (1)°

  • γ = 89.069 (1)°

  • V = 1437.80 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 296 K

  • 0.50 × 0.42 × 0.23 mm

Data collection
  • Bruker APEX DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.887, Tmax = 0.945

  • 31117 measured reflections

  • 8251 independent reflections

  • 6347 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.144

  • S = 1.07

  • 8251 reflections

  • 415 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C11B–C16B ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C5B—H5BACg4i 0.93 2.85 3.4757 (19) 126
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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. 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 (Rocío Pozas et al., 2005) as well as various CNS activities (Rana et al., 2008). The structure of 2-[5-(4-methoxyphenyl)-3-phenyl-4,5- dihydro-1H-pyrazol-1-yl]-6-methyl-1,3-benzothiazole has been reported by Fun et al. (2011). The present work describes the synthesis and crystal structure of the title compound, 1-(6-fluorobenzo-1,3-thiazol-2-yl)-3-phenyl-1H-pyrazole-4- carbaldehyde which was prepared from the reaction of 1-(6-fluoro-1,3-benzothiazol-2-yl)-2-(1-phenylethylidene)hydrazine treated with Vilsmeier-Haack reagent to obtain crystals of the title compound.

The asymmetric unit of the title compound consists of two crystallographically independent molecules A and B as shown in Fig. 1. The pyrazole rings (N2A/N3A/C8A–C10A and N2B/N3B/C8B–C10B) are approximately planar with a maximum deviation of 0.002 (2) Å for atom C8A and 0.001 (2) Å for atom C9B. The central pyrazole (N2/N3/C8–C10) ring makes dihedral angles of 6.51 (7) and 34.02 (9)°, respectively, with the terminal benzo[d]thiazole ring (S1/N1/C1–C7) system and the phenyl ring (C11–C16) for molecule A. These values are 6.41 (8) and 23.06 (9)° for molecule B. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structure (Fun et al., 2011).

In the crystal structure (Fig. 2), no classical hydrogen bonds were observed and stabilization is provided by a weak ππ interaction between the thiazoline (S1A/N1A/C1A/C6A–C7A) and the phenyl ring (C11B–C16B) [centroid-to-centroid (-1 + x, y, z) distance = 3.7069 (10) Å]. The structure is further stabilized by C—H···π interactions, involving the centroid of phenyl ring (C11B–C16B; Cg4; Table 1).

Related literature top

For the biological activity of benzothiazole 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); Rocío Pozas et al. (2005); Rana et al. (2008). For a related structure, see: Fun et al. (2011). For bond-length data, see: Allen et al. (1987).

Experimental top

1-(6-Fluorobenzo[d]thiazol-2-yl)-2-(1-phenylethylidene)hydrazine was treated with Vilsmeier-Haack reagent (DMF/POCl3: 10:1.1 ml) and was stirred at 60–65 °C for 2.5 h. It was poured into cold water and the solid that separated out by neutralization with NaHCO3 was filtered, washed with water and was then purified by column chromatography. The product was recrystallized from petroleum ether and ethyl acetate (80: 20) to yield block-shaped colorless crystals.

Refinement top

All the H atoms were positioned geometrically (C—H = 0.93 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Structure description 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. 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 (Rocío Pozas et al., 2005) as well as various CNS activities (Rana et al., 2008). The structure of 2-[5-(4-methoxyphenyl)-3-phenyl-4,5- dihydro-1H-pyrazol-1-yl]-6-methyl-1,3-benzothiazole has been reported by Fun et al. (2011). The present work describes the synthesis and crystal structure of the title compound, 1-(6-fluorobenzo-1,3-thiazol-2-yl)-3-phenyl-1H-pyrazole-4- carbaldehyde which was prepared from the reaction of 1-(6-fluoro-1,3-benzothiazol-2-yl)-2-(1-phenylethylidene)hydrazine treated with Vilsmeier-Haack reagent to obtain crystals of the title compound.

The asymmetric unit of the title compound consists of two crystallographically independent molecules A and B as shown in Fig. 1. The pyrazole rings (N2A/N3A/C8A–C10A and N2B/N3B/C8B–C10B) are approximately planar with a maximum deviation of 0.002 (2) Å for atom C8A and 0.001 (2) Å for atom C9B. The central pyrazole (N2/N3/C8–C10) ring makes dihedral angles of 6.51 (7) and 34.02 (9)°, respectively, with the terminal benzo[d]thiazole ring (S1/N1/C1–C7) system and the phenyl ring (C11–C16) for molecule A. These values are 6.41 (8) and 23.06 (9)° for molecule B. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structure (Fun et al., 2011).

In the crystal structure (Fig. 2), no classical hydrogen bonds were observed and stabilization is provided by a weak ππ interaction between the thiazoline (S1A/N1A/C1A/C6A–C7A) and the phenyl ring (C11B–C16B) [centroid-to-centroid (-1 + x, y, z) distance = 3.7069 (10) Å]. The structure is further stabilized by C—H···π interactions, involving the centroid of phenyl ring (C11B–C16B; Cg4; Table 1).

For the biological activity of benzothiazole 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); Rocío Pozas et al. (2005); Rana et al. (2008). For a related structure, see: Fun et al. (2011). For bond-length data, see: Allen et al. (1987).

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing two independent molecules with atom labels and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound.
1-(6-Fluoro-1,3-benzothiazol-2-yl)-3-phenyl-1H-pyrazole-4- carbaldehyde top
Crystal data top
C17H10FN3OSZ = 4
Mr = 323.34F(000) = 664
Triclinic, P1Dx = 1.494 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0994 (3) ÅCell parameters from 9988 reflections
b = 13.6566 (4) Åθ = 2.6–32.6°
c = 13.8472 (5) ŵ = 0.24 mm1
α = 70.393 (1)°T = 296 K
β = 85.264 (1)°Block, colourless
γ = 89.069 (1)°0.50 × 0.42 × 0.23 mm
V = 1437.80 (9) Å3
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer
8251 independent reflections
Radiation source: fine-focus sealed tube6347 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 30.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1111
Tmin = 0.887, Tmax = 0.945k = 1819
31117 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0724P)2 + 0.2771P]
where P = (Fo2 + 2Fc2)/3
8251 reflections(Δ/σ)max < 0.001
415 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C17H10FN3OSγ = 89.069 (1)°
Mr = 323.34V = 1437.80 (9) Å3
Triclinic, P1Z = 4
a = 8.0994 (3) ÅMo Kα radiation
b = 13.6566 (4) ŵ = 0.24 mm1
c = 13.8472 (5) ÅT = 296 K
α = 70.393 (1)°0.50 × 0.42 × 0.23 mm
β = 85.264 (1)°
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer
8251 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
6347 reflections with I > 2σ(I)
Tmin = 0.887, Tmax = 0.945Rint = 0.024
31117 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.144H-atom parameters constrained
S = 1.07Δρmax = 0.31 e Å3
8251 reflectionsΔρmin = 0.24 e Å3
415 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
xyzUiso*/Ueq
S1A0.67133 (5)0.82264 (3)0.08427 (3)0.04991 (12)
F1A0.35358 (17)0.50191 (10)0.07601 (10)0.0780 (4)
O1A0.7893 (3)1.00042 (13)0.48380 (11)0.0904 (5)
N1A0.57383 (16)0.74868 (9)0.27972 (9)0.0436 (3)
N2A0.72337 (16)0.90516 (9)0.23250 (9)0.0419 (3)
N3A0.79295 (16)0.98890 (9)0.15536 (9)0.0426 (3)
C1A0.51321 (18)0.68136 (10)0.23461 (11)0.0403 (3)
C2A0.4170 (2)0.59282 (12)0.28661 (13)0.0490 (3)
H2AA0.38890.57450.35690.059*
C3A0.3639 (2)0.53261 (12)0.23229 (14)0.0538 (4)
H3AA0.29940.47330.26530.065*
C4A0.4084 (2)0.56223 (13)0.12799 (14)0.0531 (4)
C5A0.5024 (2)0.64888 (13)0.07234 (13)0.0510 (4)
H5AA0.52940.66640.00200.061*
C6A0.55449 (18)0.70860 (11)0.12851 (11)0.0420 (3)
C7A0.65299 (18)0.82331 (11)0.20963 (11)0.0404 (3)
C8A0.72749 (19)0.91363 (12)0.32581 (11)0.0446 (3)
H8AA0.68620.86570.38810.054*
C9A0.80446 (19)1.00673 (11)0.31171 (11)0.0439 (3)
C10A0.84341 (18)1.05089 (11)0.20331 (11)0.0406 (3)
C11A0.92322 (19)1.15176 (11)0.14425 (11)0.0416 (3)
C12A0.8739 (2)1.20843 (12)0.04738 (11)0.0473 (3)
H12A0.79251.18170.01930.057*
C13A0.9459 (2)1.30451 (13)0.00723 (13)0.0537 (4)
H13A0.91441.34140.07250.064*
C14A1.0642 (2)1.34576 (13)0.03492 (14)0.0561 (4)
H14A1.11001.41110.00120.067*
C15A1.1144 (2)1.29020 (13)0.13046 (14)0.0557 (4)
H15A1.19491.31780.15840.067*
C16A1.0452 (2)1.19319 (12)0.18507 (13)0.0497 (3)
H16A1.08041.15560.24920.060*
C17A0.8236 (3)1.04889 (15)0.39380 (14)0.0595 (4)
H17A0.86421.11650.37620.071*
S1B0.85368 (6)0.49438 (3)0.24460 (3)0.05176 (12)
F1B0.50654 (18)0.19249 (10)0.22056 (12)0.0855 (4)
O1B0.8877 (2)0.71038 (14)0.62541 (10)0.0816 (5)
N1B0.71374 (18)0.43506 (10)0.43233 (10)0.0501 (3)
N2B0.88353 (17)0.58379 (10)0.38940 (10)0.0473 (3)
N3B0.98472 (17)0.65462 (10)0.31604 (10)0.0463 (3)
C1B0.65907 (19)0.36730 (12)0.38591 (12)0.0470 (3)
C2B0.5465 (2)0.28536 (14)0.43263 (15)0.0589 (4)
H2BA0.50570.27070.50080.071*
C3B0.4968 (2)0.22667 (14)0.37629 (17)0.0644 (5)
H3BA0.42200.17180.40600.077*
C4B0.5595 (2)0.25033 (14)0.27492 (17)0.0613 (4)
C5B0.6719 (2)0.32944 (13)0.22546 (15)0.0557 (4)
H5BA0.71240.34300.15740.067*
C6B0.72117 (19)0.38764 (11)0.28344 (12)0.0470 (3)
C7B0.8123 (2)0.50277 (12)0.36636 (11)0.0456 (3)
C8B0.8587 (2)0.60645 (13)0.47682 (12)0.0510 (4)
H8BA0.79430.56850.53600.061*
C9B0.9459 (2)0.69574 (12)0.46208 (11)0.0471 (3)
C10B1.02340 (19)0.72353 (12)0.35926 (11)0.0435 (3)
C11B1.12870 (19)0.81364 (11)0.30056 (11)0.0429 (3)
C12B1.1391 (2)0.84764 (13)0.19371 (12)0.0515 (4)
H12B1.08080.81230.16020.062*
C13B1.2353 (3)0.93346 (14)0.13668 (13)0.0596 (4)
H13B1.24170.95510.06520.072*
C14B1.3220 (2)0.98730 (13)0.18518 (14)0.0571 (4)
H14B1.38671.04500.14670.069*
C15B1.3118 (2)0.95467 (14)0.29113 (14)0.0561 (4)
H15B1.36830.99130.32420.067*
C16B1.2181 (2)0.86785 (14)0.34855 (13)0.0516 (4)
H16B1.21480.84540.42000.062*
C17B0.9424 (2)0.74922 (16)0.53715 (13)0.0588 (4)
H17B0.98440.81680.51600.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0640 (3)0.0439 (2)0.03977 (19)0.01902 (16)0.00701 (16)0.01313 (15)
F1A0.0888 (9)0.0728 (7)0.0857 (8)0.0342 (6)0.0022 (6)0.0449 (6)
O1A0.1431 (16)0.0870 (11)0.0442 (7)0.0231 (10)0.0030 (8)0.0259 (7)
N1A0.0500 (7)0.0381 (6)0.0409 (6)0.0074 (5)0.0011 (5)0.0118 (5)
N2A0.0480 (7)0.0372 (6)0.0393 (6)0.0097 (5)0.0003 (5)0.0117 (5)
N3A0.0519 (7)0.0356 (6)0.0389 (6)0.0107 (5)0.0024 (5)0.0115 (5)
C1A0.0415 (7)0.0334 (6)0.0437 (7)0.0043 (5)0.0005 (5)0.0106 (5)
C2A0.0535 (9)0.0396 (7)0.0485 (8)0.0103 (6)0.0061 (6)0.0098 (6)
C3A0.0513 (9)0.0413 (8)0.0653 (10)0.0146 (6)0.0036 (7)0.0143 (7)
C4A0.0516 (9)0.0478 (8)0.0667 (10)0.0104 (7)0.0039 (7)0.0279 (8)
C5A0.0564 (9)0.0506 (8)0.0479 (8)0.0113 (7)0.0011 (7)0.0199 (7)
C6A0.0449 (7)0.0376 (7)0.0423 (7)0.0069 (5)0.0013 (5)0.0127 (5)
C7A0.0441 (7)0.0365 (6)0.0403 (7)0.0054 (5)0.0003 (5)0.0130 (5)
C8A0.0508 (8)0.0418 (7)0.0390 (7)0.0071 (6)0.0019 (6)0.0106 (6)
C9A0.0511 (8)0.0423 (7)0.0395 (7)0.0059 (6)0.0036 (6)0.0148 (6)
C10A0.0447 (7)0.0360 (6)0.0414 (7)0.0047 (5)0.0011 (5)0.0139 (5)
C11A0.0476 (8)0.0350 (6)0.0433 (7)0.0061 (5)0.0027 (5)0.0158 (5)
C12A0.0548 (9)0.0464 (8)0.0422 (7)0.0091 (6)0.0001 (6)0.0174 (6)
C13A0.0658 (10)0.0469 (8)0.0436 (8)0.0075 (7)0.0023 (7)0.0100 (6)
C14A0.0666 (10)0.0429 (8)0.0555 (9)0.0155 (7)0.0095 (7)0.0150 (7)
C15A0.0569 (10)0.0516 (9)0.0602 (10)0.0178 (7)0.0006 (7)0.0211 (8)
C16A0.0547 (9)0.0441 (8)0.0501 (8)0.0100 (6)0.0060 (7)0.0147 (6)
C17A0.0771 (12)0.0576 (10)0.0486 (9)0.0107 (8)0.0045 (8)0.0238 (8)
S1B0.0601 (2)0.0447 (2)0.0457 (2)0.01154 (16)0.01026 (16)0.01161 (16)
F1B0.0844 (9)0.0729 (8)0.1136 (11)0.0191 (6)0.0036 (7)0.0501 (7)
O1B0.0912 (11)0.1110 (12)0.0449 (7)0.0069 (9)0.0001 (7)0.0300 (7)
N1B0.0538 (8)0.0477 (7)0.0411 (7)0.0078 (6)0.0009 (5)0.0055 (5)
N2B0.0536 (7)0.0438 (7)0.0395 (6)0.0079 (5)0.0017 (5)0.0082 (5)
N3B0.0508 (7)0.0423 (6)0.0416 (6)0.0077 (5)0.0038 (5)0.0100 (5)
C1B0.0436 (8)0.0418 (7)0.0485 (8)0.0033 (6)0.0005 (6)0.0064 (6)
C2B0.0522 (9)0.0516 (9)0.0618 (10)0.0110 (7)0.0068 (7)0.0064 (8)
C3B0.0509 (10)0.0503 (9)0.0847 (13)0.0122 (7)0.0045 (8)0.0147 (9)
C4B0.0535 (10)0.0500 (9)0.0849 (13)0.0030 (7)0.0055 (9)0.0284 (9)
C5B0.0569 (10)0.0497 (9)0.0614 (10)0.0032 (7)0.0031 (7)0.0217 (8)
C6B0.0461 (8)0.0388 (7)0.0506 (8)0.0020 (6)0.0022 (6)0.0093 (6)
C7B0.0476 (8)0.0416 (7)0.0416 (7)0.0036 (6)0.0012 (6)0.0064 (6)
C8B0.0564 (9)0.0551 (9)0.0362 (7)0.0053 (7)0.0006 (6)0.0087 (6)
C9B0.0497 (8)0.0508 (8)0.0371 (7)0.0019 (6)0.0037 (6)0.0097 (6)
C10B0.0444 (7)0.0441 (7)0.0395 (7)0.0004 (6)0.0023 (5)0.0110 (6)
C11B0.0448 (7)0.0405 (7)0.0432 (7)0.0016 (5)0.0007 (5)0.0141 (6)
C12B0.0639 (10)0.0483 (8)0.0436 (8)0.0104 (7)0.0013 (7)0.0182 (6)
C13B0.0790 (12)0.0520 (9)0.0446 (9)0.0138 (8)0.0043 (8)0.0134 (7)
C14B0.0620 (10)0.0462 (8)0.0606 (10)0.0116 (7)0.0028 (8)0.0157 (7)
C15B0.0537 (9)0.0565 (9)0.0639 (10)0.0101 (7)0.0042 (7)0.0274 (8)
C16B0.0532 (9)0.0570 (9)0.0458 (8)0.0044 (7)0.0055 (6)0.0182 (7)
C17B0.0604 (10)0.0719 (11)0.0472 (9)0.0051 (8)0.0039 (7)0.0241 (8)
Geometric parameters (Å, º) top
S1A—C7A1.7331 (15)S1B—C6B1.7307 (16)
S1A—C6A1.7344 (14)S1B—C7B1.7330 (16)
F1A—C4A1.3626 (18)F1B—C4B1.356 (2)
O1A—C17A1.210 (2)O1B—C17B1.206 (2)
N1A—C7A1.2831 (17)N1B—C7B1.2896 (19)
N1A—C1A1.3882 (18)N1B—C1B1.387 (2)
N2A—C8A1.3385 (19)N2B—C8B1.346 (2)
N2A—N3A1.3667 (15)N2B—N3B1.3668 (16)
N2A—C7A1.4010 (18)N2B—C7B1.395 (2)
N3A—C10A1.3258 (18)N3B—C10B1.327 (2)
C1A—C2A1.3934 (19)C1B—C2B1.397 (2)
C1A—C6A1.402 (2)C1B—C6B1.402 (2)
C2A—C3A1.381 (2)C2B—C3B1.377 (3)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.381 (2)C3B—C4B1.384 (3)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.376 (2)C4B—C5B1.378 (2)
C5A—C6A1.393 (2)C5B—C6B1.388 (2)
C5A—H5AA0.9300C5B—H5BA0.9300
C8A—C9A1.372 (2)C8B—C9B1.366 (2)
C8A—H8AA0.9300C8B—H8BA0.9300
C9A—C10A1.427 (2)C9B—C10B1.436 (2)
C9A—C17A1.456 (2)C9B—C17B1.456 (2)
C10A—C11A1.4730 (19)C10B—C11B1.467 (2)
C11A—C12A1.393 (2)C11B—C12B1.390 (2)
C11A—C16A1.393 (2)C11B—C16B1.393 (2)
C12A—C13A1.385 (2)C12B—C13B1.382 (2)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.381 (3)C13B—C14B1.383 (2)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.377 (3)C14B—C15B1.378 (3)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.387 (2)C15B—C16B1.382 (2)
C15A—H15A0.9300C15B—H15B0.9300
C16A—H16A0.9300C16B—H16B0.9300
C17A—H17A0.9300C17B—H17B0.9300
C7A—S1A—C6A87.24 (7)C6B—S1B—C7B87.38 (7)
C7A—N1A—C1A108.70 (12)C7B—N1B—C1B108.42 (13)
C8A—N2A—N3A113.04 (12)C8B—N2B—N3B112.64 (13)
C8A—N2A—C7A126.58 (12)C8B—N2B—C7B127.64 (13)
N3A—N2A—C7A120.35 (11)N3B—N2B—C7B119.62 (13)
C10A—N3A—N2A104.40 (11)C10B—N3B—N2B104.84 (12)
N1A—C1A—C2A124.95 (13)N1B—C1B—C2B124.95 (15)
N1A—C1A—C6A114.96 (12)N1B—C1B—C6B115.21 (13)
C2A—C1A—C6A120.08 (14)C2B—C1B—C6B119.80 (16)
C3A—C2A—C1A119.11 (15)C3B—C2B—C1B119.08 (17)
C3A—C2A—H2AA120.4C3B—C2B—H2BA120.5
C1A—C2A—H2AA120.4C1B—C2B—H2BA120.5
C2A—C3A—C4A118.72 (14)C2B—C3B—C4B119.22 (16)
C2A—C3A—H3AA120.6C2B—C3B—H3BA120.4
C4A—C3A—H3AA120.6C4B—C3B—H3BA120.4
F1A—C4A—C5A117.53 (16)F1B—C4B—C5B117.80 (18)
F1A—C4A—C3A117.59 (14)F1B—C4B—C3B118.10 (17)
C5A—C4A—C3A124.87 (15)C5B—C4B—C3B124.10 (18)
C4A—C5A—C6A115.49 (15)C4B—C5B—C6B115.96 (17)
C4A—C5A—H5AA122.3C4B—C5B—H5BA122.0
C6A—C5A—H5AA122.3C6B—C5B—H5BA122.0
C5A—C6A—C1A121.72 (13)C5B—C6B—C1B121.84 (15)
C5A—C6A—S1A128.22 (12)C5B—C6B—S1B128.06 (13)
C1A—C6A—S1A110.06 (10)C1B—C6B—S1B110.06 (12)
N1A—C7A—N2A121.30 (13)N1B—C7B—N2B121.97 (15)
N1A—C7A—S1A119.01 (11)N1B—C7B—S1B118.92 (13)
N2A—C7A—S1A119.69 (10)N2B—C7B—S1B119.10 (11)
N2A—C8A—C9A106.68 (13)N2B—C8B—C9B106.95 (14)
N2A—C8A—H8AA126.7N2B—C8B—H8BA126.5
C9A—C8A—H8AA126.7C9B—C8B—H8BA126.5
C8A—C9A—C10A105.00 (13)C8B—C9B—C10B105.11 (14)
C8A—C9A—C17A124.08 (14)C8B—C9B—C17B123.68 (15)
C10A—C9A—C17A130.72 (14)C10B—C9B—C17B131.06 (15)
N3A—C10A—C9A110.88 (12)N3B—C10B—C9B110.46 (13)
N3A—C10A—C11A120.38 (12)N3B—C10B—C11B119.89 (13)
C9A—C10A—C11A128.72 (13)C9B—C10B—C11B129.63 (14)
C12A—C11A—C16A119.04 (13)C12B—C11B—C16B118.35 (14)
C12A—C11A—C10A120.05 (13)C12B—C11B—C10B119.60 (14)
C16A—C11A—C10A120.88 (14)C16B—C11B—C10B122.04 (14)
C13A—C12A—C11A120.16 (15)C13B—C12B—C11B120.69 (15)
C13A—C12A—H12A119.9C13B—C12B—H12B119.7
C11A—C12A—H12A119.9C11B—C12B—H12B119.7
C14A—C13A—C12A120.28 (16)C12B—C13B—C14B120.43 (16)
C14A—C13A—H13A119.9C12B—C13B—H13B119.8
C12A—C13A—H13A119.9C14B—C13B—H13B119.8
C15A—C14A—C13A120.04 (15)C15B—C14B—C13B119.39 (16)
C15A—C14A—H14A120.0C15B—C14B—H14B120.3
C13A—C14A—H14A120.0C13B—C14B—H14B120.3
C14A—C15A—C16A120.16 (16)C14B—C15B—C16B120.42 (16)
C14A—C15A—H15A119.9C14B—C15B—H15B119.8
C16A—C15A—H15A119.9C16B—C15B—H15B119.8
C15A—C16A—C11A120.30 (15)C15B—C16B—C11B120.69 (15)
C15A—C16A—H16A119.9C15B—C16B—H16B119.7
C11A—C16A—H16A119.9C11B—C16B—H16B119.7
O1A—C17A—C9A123.28 (17)O1B—C17B—C9B123.33 (19)
O1A—C17A—H17A118.4O1B—C17B—H17B118.3
C9A—C17A—H17A118.4C9B—C17B—H17B118.3
C8A—N2A—N3A—C10A0.64 (17)C8B—N2B—N3B—C10B0.18 (18)
C7A—N2A—N3A—C10A178.86 (13)C7B—N2B—N3B—C10B176.45 (14)
C7A—N1A—C1A—C2A178.13 (15)C7B—N1B—C1B—C2B177.98 (16)
C7A—N1A—C1A—C6A1.36 (19)C7B—N1B—C1B—C6B0.1 (2)
N1A—C1A—C2A—C3A179.70 (15)N1B—C1B—C2B—C3B177.10 (16)
C6A—C1A—C2A—C3A0.2 (2)C6B—C1B—C2B—C3B0.9 (3)
C1A—C2A—C3A—C4A0.1 (3)C1B—C2B—C3B—C4B0.0 (3)
C2A—C3A—C4A—F1A179.57 (16)C2B—C3B—C4B—F1B178.94 (17)
C2A—C3A—C4A—C5A0.4 (3)C2B—C3B—C4B—C5B0.8 (3)
F1A—C4A—C5A—C6A179.47 (15)F1B—C4B—C5B—C6B179.16 (16)
C3A—C4A—C5A—C6A0.3 (3)C3B—C4B—C5B—C6B0.5 (3)
C4A—C5A—C6A—C1A0.1 (2)C4B—C5B—C6B—C1B0.4 (3)
C4A—C5A—C6A—S1A179.15 (13)C4B—C5B—C6B—S1B177.55 (14)
N1A—C1A—C6A—C5A179.85 (15)N1B—C1B—C6B—C5B177.06 (15)
C2A—C1A—C6A—C5A0.3 (2)C2B—C1B—C6B—C5B1.1 (2)
N1A—C1A—C6A—S1A0.51 (17)N1B—C1B—C6B—S1B0.56 (18)
C2A—C1A—C6A—S1A179.01 (12)C2B—C1B—C6B—S1B178.70 (13)
C7A—S1A—C6A—C5A178.96 (16)C7B—S1B—C6B—C5B176.70 (17)
C7A—S1A—C6A—C1A0.33 (11)C7B—S1B—C6B—C1B0.73 (12)
C1A—N1A—C7A—N2A177.85 (13)C1B—N1B—C7B—N2B177.88 (14)
C1A—N1A—C7A—S1A1.70 (17)C1B—N1B—C7B—S1B0.70 (19)
C8A—N2A—C7A—N1A4.4 (2)C8B—N2B—C7B—N1B2.7 (3)
N3A—N2A—C7A—N1A173.56 (13)N3B—N2B—C7B—N1B178.78 (15)
C8A—N2A—C7A—S1A176.06 (12)C8B—N2B—C7B—S1B175.86 (13)
N3A—N2A—C7A—S1A5.98 (19)N3B—N2B—C7B—S1B0.2 (2)
C6A—S1A—C7A—N1A1.24 (13)C6B—S1B—C7B—N1B0.88 (14)
C6A—S1A—C7A—N2A178.32 (13)C6B—S1B—C7B—N2B177.74 (14)
N3A—N2A—C8A—C9A0.53 (18)N3B—N2B—C8B—C9B0.05 (19)
C7A—N2A—C8A—C9A178.62 (15)C7B—N2B—C8B—C9B176.25 (15)
N2A—C8A—C9A—C10A0.20 (17)N2B—C8B—C9B—C10B0.10 (18)
N2A—C8A—C9A—C17A175.54 (16)N2B—C8B—C9B—C17B176.03 (16)
N2A—N3A—C10A—C9A0.49 (17)N2B—N3B—C10B—C9B0.24 (17)
N2A—N3A—C10A—C11A178.81 (13)N2B—N3B—C10B—C11B178.39 (13)
C8A—C9A—C10A—N3A0.19 (18)C8B—C9B—C10B—N3B0.22 (19)
C17A—C9A—C10A—N3A174.72 (17)C17B—C9B—C10B—N3B175.73 (17)
C8A—C9A—C10A—C11A178.33 (15)C8B—C9B—C10B—C11B178.24 (16)
C17A—C9A—C10A—C11A3.4 (3)C17B—C9B—C10B—C11B2.7 (3)
N3A—C10A—C11A—C12A34.0 (2)N3B—C10B—C11B—C12B22.9 (2)
C9A—C10A—C11A—C12A143.94 (16)C9B—C10B—C11B—C12B155.43 (17)
N3A—C10A—C11A—C16A147.70 (15)N3B—C10B—C11B—C16B157.91 (16)
C9A—C10A—C11A—C16A34.3 (2)C9B—C10B—C11B—C16B23.8 (3)
C16A—C11A—C12A—C13A0.1 (2)C16B—C11B—C12B—C13B0.3 (3)
C10A—C11A—C12A—C13A178.39 (14)C10B—C11B—C12B—C13B178.89 (16)
C11A—C12A—C13A—C14A1.5 (3)C11B—C12B—C13B—C14B0.4 (3)
C12A—C13A—C14A—C15A1.7 (3)C12B—C13B—C14B—C15B0.0 (3)
C13A—C14A—C15A—C16A0.7 (3)C13B—C14B—C15B—C16B1.1 (3)
C14A—C15A—C16A—C11A0.7 (3)C14B—C15B—C16B—C11B1.9 (3)
C12A—C11A—C16A—C15A1.0 (2)C12B—C11B—C16B—C15B1.4 (3)
C10A—C11A—C16A—C15A177.30 (15)C10B—C11B—C16B—C15B177.75 (15)
C8A—C9A—C17A—O1A8.3 (3)C8B—C9B—C17B—O1B14.1 (3)
C10A—C9A—C17A—O1A177.6 (2)C10B—C9B—C17B—O1B171.10 (19)
Hydrogen-bond geometry (Å, º) top
Cg4 is the centroid of the C11B–C16B ring.
D—H···AD—HH···AD···AD—H···A
C5B—H5BA···Cg4i0.932.853.4757 (19)126
Symmetry code: (i) x, y1, z.

Experimental details

Crystal data
Chemical formulaC17H10FN3OS
Mr323.34
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)8.0994 (3), 13.6566 (4), 13.8472 (5)
α, β, γ (°)70.393 (1), 85.264 (1), 89.069 (1)
V3)1437.80 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.50 × 0.42 × 0.23
Data collection
DiffractometerBruker APEX DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.887, 0.945
No. of measured, independent and
observed [I > 2σ(I)] reflections
31117, 8251, 6347
Rint0.024
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.144, 1.07
No. of reflections8251
No. of parameters415
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.24

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

Hydrogen-bond geometry (Å, º) top
Cg4 is the centroid of the C11B–C16B ring.
D—H···AD—HH···AD···AD—H···A
C5B—H5BA···Cg4i0.932.853.4757 (19)126
Symmetry code: (i) x, y1, z.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). CWO also thanks the Malaysian Government and USM for the award of the post of research assistant under the Research University Grant (1001/PFIZIK/811151). HM gratefully acknowledges the School of Advanced Sciences, VIT University, Vellore, for providing facilities to carry out research.

References

First citationAllen, 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
First citationAl-Soud, Y. A., Al-Sa'doni, H., Amajaour, H. A. S. & Al-Masoudi, A. (2006). Z. Naturforsch. Teil A, 62, 523–528.  Google Scholar
First citationBowyer, P. W., Gunaratne, R. S., Grainge, 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
First citationBruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFun, H.-K., Arshad, S., Himaja, M., Munirajasekhar, D. & Sarojini, B. K. (2011). Acta Cryst. E67, o2412.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGurupadayya, B. M., Gopal, M., Padmashali, B. & Manohara, Y. N. (2008). Indian J. Pharm. Sci. 70, 572–577.  Web of Science CAS PubMed Google Scholar
First citationKini, S., Swain, S. P. & Gandhi, A. M. (2007). Indian J. Pharm. Sci. 69, 46–50.  CrossRef CAS Google Scholar
First citationMittal, S., Samottra, M. K., Kaur, J. & Gita, S. (2007). Phosphorus Sulfur Silicon Relat. Elem. 9, 2105–2113.  Web of Science CrossRef Google Scholar
First citationMunirajasekhar, D., Himaja, M. & Sunil, V. M. (2011). Int. Res. J. Pharm. 2, 114–117.  CAS Google Scholar
First citationPozas, R., Carballo, J., Castro, C. & Rubio, J. (2005). Bioorg. Med. Chem. Lett. 15, 1417–1421.  Web of Science CrossRef PubMed CAS Google Scholar
First citationRana, A., Siddiqui, N. & Khan, S. (2008). Eur. J. Med. Chem. 43, 1114–1122.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds