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

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890

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

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[Al-Soud, Y. A., Al-Sa'doni, H., Amajaour, H. A. S. & Al-Masoudi, N. A. (2006). Z. Naturforsch. Teil B, 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., 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.]); Mittal et al. (2007[Mittal, S., Samottra, M. K., Kaur, J. & Gita, S. (2007). Phosphorus Sulfur Silicon Relat. Elem. 182, 2105-2113.]); 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 standard 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.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12FN3S

  • Mr = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.894, Tmax = 0.965

  • 52781 measured reflections

  • 7411 independent reflections

  • 7049 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.080

  • S = 1.06

  • 7411 reflections

  • 364 parameters

  • H-atom parameters constrained

  • Δρmax = 0.46 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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⋯F1Aiv 0.95 2.52 3.289 (2) 138
C12A—H12B⋯F1Bv 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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 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.

Refinement top

The N-bound hydrogen atoms were located in a difference Fourier map and refined using a riding model with Uiso(H) = 1.2 Ueq(N) [N–H = 0.789 or 0.93 Å]. The remaining H atoms were positioned geometrically and refined using a riding model with C–H = 0.95 or 0.98 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied for the methyl group. The crystal studied was a twin with twin law, 101 0-10 00-1 and BASF = 0.301 (2). Three outliers (-3 1 7; 2 1 0; 5 0 4) were omitted in the final refinement cycles.

Structure description 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.

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
[Figure 1] Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] 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
C15H12FN3SF(000) = 1184
Mr = 285.34Dx = 1.443 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 9959 reflections
a = 28.312 (3) Åθ = 2.9–29.6°
b = 7.2952 (7) ŵ = 0.25 mm1
c = 13.0626 (13) ÅT = 100 K
β = 103.151 (2)°Block, yellow
V = 2627.2 (5) Å30.46 × 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 tube7049 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 29.7°, θmin = 0.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 3939
Tmin = 0.894, Tmax = 0.965k = 1010
52781 measured reflectionsl = 1818
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0333P)2 + 1.4375P]
where P = (Fo2 + 2Fc2)/3
7411 reflections(Δ/σ)max = 0.002
364 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C15H12FN3SV = 2627.2 (5) Å3
Mr = 285.34Z = 8
Monoclinic, P2/cMo Kα radiation
a = 28.312 (3) ŵ = 0.25 mm1
b = 7.2952 (7) ÅT = 100 K
c = 13.0626 (13) Å0.46 × 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)
Tmin = 0.894, Tmax = 0.965Rint = 0.036
52781 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.080H-atom parameters constrained
S = 1.06Δρmax = 0.46 e Å3
7411 reflectionsΔρmin = 0.43 e Å3
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
xyzUiso*/Ueq
S1A0.972160 (13)0.76932 (5)1.01810 (3)0.01518 (8)
F1A1.12593 (4)0.52213 (16)1.27187 (9)0.0279 (2)
N1A1.02856 (5)0.76694 (18)0.88368 (11)0.0153 (2)
N2A0.94918 (4)0.86931 (19)0.81485 (11)0.0164 (3)
H1NA0.95100.84610.74570.020*
N3A0.90434 (4)0.88095 (18)0.83979 (11)0.0156 (2)
C1A1.03203 (5)0.6981 (2)1.06242 (13)0.0157 (3)
C2A1.05463 (6)0.6359 (2)1.16183 (13)0.0185 (3)
H2AA1.03810.62911.21740.022*
C3A1.10265 (6)0.5845 (2)1.17516 (13)0.0197 (3)
C4A1.12836 (6)0.5918 (2)1.09697 (14)0.0197 (3)
H4AA1.16150.55621.11120.024*
C5A1.10515 (5)0.6519 (2)0.99766 (13)0.0176 (3)
H5AA1.12200.65610.94250.021*
C6A1.05651 (5)0.7064 (2)0.97977 (13)0.0142 (3)
C7A0.98479 (5)0.8033 (2)0.89425 (12)0.0141 (3)
C8A0.86838 (5)0.9481 (2)0.77176 (12)0.0151 (3)
C9A0.82091 (5)0.9398 (2)0.80292 (13)0.0154 (3)
C10A0.77909 (5)1.0154 (2)0.73955 (13)0.0190 (3)
H10B0.78111.08140.67800.023*
C11A0.73430 (5)0.9950 (2)0.76586 (14)0.0224 (3)
H11B0.70611.04820.72240.027*
C12A0.73052 (6)0.8977 (2)0.85482 (15)0.0222 (3)
H12B0.69990.88190.87160.027*
C13A0.77206 (6)0.8236 (2)0.91916 (15)0.0219 (3)
H13B0.76990.75780.98070.026*
C14A0.81679 (5)0.8455 (2)0.89382 (13)0.0180 (3)
H14B0.84500.79570.93880.022*
C15A0.87077 (6)1.0251 (2)0.66642 (14)0.0212 (3)
H15D0.90461.02730.66000.032*
H15E0.85771.15000.65990.032*
H15F0.85160.94810.61070.032*
S1B0.530131 (12)0.72187 (5)1.04747 (3)0.01352 (8)
F1B0.37853 (3)0.96714 (15)1.16254 (8)0.0242 (2)
N1B0.47380 (4)0.75091 (17)0.85933 (10)0.0135 (2)
N2B0.55248 (4)0.64677 (18)0.86209 (10)0.0154 (2)
H1NB0.54960.67290.80240.018*
N3B0.59655 (4)0.60724 (17)0.92759 (10)0.0139 (2)
C1B0.47084 (5)0.7988 (2)1.03672 (12)0.0125 (3)
C2B0.44856 (5)0.8532 (2)1.11663 (13)0.0164 (3)
H2BA0.46520.85001.18850.020*
C3B0.40115 (5)0.9118 (2)1.08580 (13)0.0161 (3)
C4B0.37534 (5)0.9174 (2)0.98252 (13)0.0160 (3)
H4BA0.34250.95720.96560.019*
C5B0.39812 (5)0.8640 (2)0.90372 (13)0.0154 (3)
H5BA0.38110.86760.83210.019*
C6B0.44636 (5)0.80470 (19)0.93059 (12)0.0125 (3)
C7B0.51744 (5)0.7067 (2)0.91009 (12)0.0131 (3)
C8B0.62998 (5)0.5364 (2)0.88735 (12)0.0143 (3)
C9B0.67655 (5)0.4959 (2)0.96244 (12)0.0133 (3)
C10B0.71024 (5)0.3762 (2)0.93491 (13)0.0181 (3)
H10A0.70370.32450.86640.022*
C11B0.75312 (5)0.3316 (2)1.00643 (15)0.0222 (3)
H11A0.77540.24870.98700.027*
C12B0.76319 (5)0.4081 (2)1.10577 (15)0.0223 (3)
H12A0.79240.37801.15480.027*
C13B0.73027 (6)0.5300 (2)1.13402 (13)0.0208 (3)
H13A0.73730.58321.20220.025*
C14B0.68728 (5)0.5737 (2)1.06267 (13)0.0173 (3)
H14A0.66510.65701.08230.021*
C15B0.62514 (6)0.4894 (2)0.77311 (13)0.0192 (3)
H15A0.59360.53180.73230.029*
H15B0.62760.35630.76550.029*
H15C0.65110.54960.74720.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.01302 (15)0.01712 (18)0.01631 (19)0.00009 (13)0.00523 (13)0.00027 (13)
F1A0.0272 (5)0.0317 (6)0.0211 (5)0.0061 (4)0.0024 (4)0.0071 (5)
N1A0.0138 (5)0.0159 (6)0.0158 (6)0.0004 (5)0.0027 (5)0.0006 (5)
N2A0.0130 (5)0.0205 (6)0.0160 (6)0.0019 (5)0.0040 (5)0.0003 (5)
N3A0.0135 (5)0.0169 (6)0.0166 (6)0.0009 (4)0.0039 (5)0.0002 (5)
C1A0.0142 (6)0.0144 (7)0.0184 (7)0.0004 (5)0.0038 (5)0.0001 (6)
C2A0.0204 (7)0.0180 (7)0.0173 (7)0.0005 (6)0.0050 (6)0.0018 (6)
C3A0.0204 (7)0.0177 (7)0.0183 (8)0.0017 (6)0.0012 (6)0.0020 (6)
C4A0.0156 (6)0.0172 (7)0.0248 (8)0.0021 (5)0.0020 (6)0.0002 (6)
C5A0.0143 (6)0.0160 (7)0.0228 (8)0.0007 (5)0.0051 (6)0.0003 (6)
C6A0.0138 (6)0.0122 (6)0.0168 (7)0.0000 (5)0.0041 (5)0.0005 (5)
C7A0.0148 (6)0.0131 (6)0.0148 (7)0.0014 (5)0.0045 (5)0.0008 (5)
C8A0.0150 (6)0.0136 (7)0.0167 (7)0.0010 (5)0.0033 (5)0.0021 (6)
C9A0.0134 (6)0.0130 (6)0.0192 (7)0.0010 (5)0.0025 (5)0.0023 (6)
C10A0.0177 (6)0.0190 (7)0.0192 (7)0.0031 (6)0.0017 (6)0.0005 (6)
C11A0.0137 (6)0.0231 (8)0.0284 (9)0.0046 (6)0.0008 (6)0.0029 (7)
C12A0.0151 (6)0.0216 (8)0.0310 (9)0.0010 (6)0.0073 (6)0.0037 (7)
C13A0.0191 (7)0.0200 (7)0.0282 (9)0.0011 (6)0.0085 (6)0.0008 (7)
C14A0.0145 (6)0.0176 (7)0.0217 (8)0.0022 (5)0.0035 (6)0.0001 (6)
C15A0.0192 (7)0.0245 (8)0.0204 (8)0.0045 (6)0.0056 (6)0.0025 (6)
S1B0.01062 (15)0.01609 (17)0.01314 (17)0.00098 (12)0.00124 (13)0.00005 (13)
F1B0.0191 (4)0.0361 (6)0.0192 (5)0.0064 (4)0.0078 (4)0.0052 (4)
N1B0.0113 (5)0.0168 (6)0.0123 (6)0.0002 (4)0.0025 (4)0.0001 (5)
N2B0.0122 (5)0.0198 (6)0.0143 (6)0.0038 (5)0.0034 (5)0.0009 (5)
N3B0.0119 (5)0.0146 (6)0.0146 (6)0.0007 (4)0.0018 (4)0.0011 (5)
C1B0.0108 (5)0.0133 (6)0.0129 (6)0.0003 (5)0.0016 (5)0.0014 (5)
C2B0.0156 (6)0.0201 (7)0.0131 (7)0.0000 (5)0.0026 (5)0.0015 (6)
C3B0.0158 (6)0.0181 (7)0.0161 (7)0.0009 (5)0.0069 (5)0.0027 (6)
C4B0.0115 (6)0.0163 (7)0.0206 (7)0.0016 (5)0.0043 (5)0.0008 (6)
C5B0.0129 (6)0.0165 (7)0.0164 (7)0.0008 (5)0.0024 (5)0.0012 (6)
C6B0.0126 (6)0.0125 (6)0.0127 (6)0.0007 (5)0.0036 (5)0.0011 (5)
C7B0.0130 (6)0.0130 (6)0.0127 (7)0.0006 (5)0.0016 (5)0.0000 (5)
C8B0.0128 (6)0.0146 (7)0.0157 (7)0.0005 (5)0.0036 (5)0.0016 (6)
C9B0.0120 (6)0.0139 (6)0.0139 (7)0.0003 (5)0.0030 (5)0.0028 (5)
C10B0.0154 (6)0.0175 (7)0.0211 (8)0.0019 (5)0.0036 (6)0.0006 (6)
C11B0.0153 (6)0.0191 (7)0.0313 (9)0.0035 (5)0.0032 (6)0.0025 (7)
C12B0.0154 (6)0.0212 (8)0.0275 (9)0.0008 (6)0.0009 (6)0.0056 (7)
C13B0.0189 (7)0.0252 (8)0.0167 (7)0.0023 (6)0.0004 (6)0.0021 (6)
C14B0.0159 (6)0.0200 (7)0.0166 (7)0.0002 (5)0.0047 (5)0.0011 (6)
C15B0.0190 (6)0.0244 (8)0.0140 (7)0.0069 (6)0.0032 (6)0.0016 (6)
Geometric parameters (Å, º) top
S1A—C1A1.7414 (15)S1B—C1B1.7451 (15)
S1A—C7A1.7521 (16)S1B—C7B1.7518 (16)
F1A—C3A1.3632 (19)F1B—C3B1.3674 (17)
N1A—C7A1.3051 (19)N1B—C7B1.3029 (18)
N1A—C6A1.395 (2)N1B—C6B1.3976 (19)
N2A—C7A1.3594 (19)N2B—C7B1.3608 (18)
N2A—N3A1.3831 (17)N2B—N3B1.3735 (17)
N2A—H1NA0.9319N2B—H1NB0.7882
N3A—C8A1.2862 (19)N3B—C8B1.2906 (19)
C1A—C2A1.387 (2)C1B—C2B1.394 (2)
C1A—C6A1.411 (2)C1B—C6B1.403 (2)
C2A—C3A1.383 (2)C2B—C3B1.379 (2)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.384 (2)C3B—C4B1.381 (2)
C4A—C5A1.385 (2)C4B—C5B1.389 (2)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.401 (2)C5B—C6B1.3989 (19)
C5A—H5AA0.9500C5B—H5BA0.9500
C8A—C9A1.492 (2)C8B—C9B1.4831 (19)
C8A—C15A1.502 (2)C8B—C15B1.507 (2)
C9A—C10A1.395 (2)C9B—C14B1.396 (2)
C9A—C14A1.400 (2)C9B—C10B1.399 (2)
C10A—C11A1.395 (2)C10B—C11B1.391 (2)
C10A—H10B0.9500C10B—H10A0.9500
C11A—C12A1.386 (3)C11B—C12B1.381 (3)
C11A—H11B0.9500C11B—H11A0.9500
C12A—C13A1.390 (2)C12B—C13B1.397 (2)
C12A—H12B0.9500C12B—H12A0.9500
C13A—C14A1.389 (2)C13B—C14B1.391 (2)
C13A—H13B0.9500C13B—H13A0.9500
C14A—H14B0.9500C14B—H14A0.9500
C15A—H15D0.9800C15B—H15A0.9800
C15A—H15E0.9800C15B—H15B0.9800
C15A—H15F0.9800C15B—H15C0.9800
C1A—S1A—C7A87.80 (7)C1B—S1B—C7B88.19 (7)
C7A—N1A—C6A109.10 (13)C7B—N1B—C6B109.69 (13)
C7A—N2A—N3A113.78 (13)C7B—N2B—N3B115.76 (12)
C7A—N2A—H1NA118.6C7B—N2B—H1NB117.1
N3A—N2A—H1NA119.8N3B—N2B—H1NB122.8
C8A—N3A—N2A119.03 (13)C8B—N3B—N2B118.47 (13)
C2A—C1A—C6A121.90 (14)C2B—C1B—C6B121.68 (13)
C2A—C1A—S1A128.01 (12)C2B—C1B—S1B128.46 (12)
C6A—C1A—S1A110.08 (12)C6B—C1B—S1B109.84 (11)
C3A—C2A—C1A115.95 (15)C3B—C2B—C1B116.47 (14)
C3A—C2A—H2AA122.0C3B—C2B—H2BA121.8
C1A—C2A—H2AA122.0C1B—C2B—H2BA121.8
F1A—C3A—C2A117.48 (15)F1B—C3B—C2B117.68 (14)
F1A—C3A—C4A118.20 (14)F1B—C3B—C4B118.38 (13)
C2A—C3A—C4A124.32 (15)C2B—C3B—C4B123.93 (14)
C3A—C4A—C5A119.11 (14)C3B—C4B—C5B118.94 (13)
C3A—C4A—H4AA120.4C3B—C4B—H4BA120.5
C5A—C4A—H4AA120.4C5B—C4B—H4BA120.5
C4A—C5A—C6A119.00 (15)C4B—C5B—C6B119.48 (14)
C4A—C5A—H5AA120.5C4B—C5B—H5BA120.3
C6A—C5A—H5AA120.5C6B—C5B—H5BA120.3
N1A—C6A—C5A125.09 (14)N1B—C6B—C5B125.34 (14)
N1A—C6A—C1A115.19 (13)N1B—C6B—C1B115.16 (12)
C5A—C6A—C1A119.71 (15)C5B—C6B—C1B119.49 (14)
N1A—C7A—N2A123.27 (14)N1B—C7B—N2B123.47 (14)
N1A—C7A—S1A117.84 (12)N1B—C7B—S1B117.10 (11)
N2A—C7A—S1A118.87 (11)N2B—C7B—S1B119.42 (11)
N3A—C8A—C9A114.63 (14)N3B—C8B—C9B115.75 (13)
N3A—C8A—C15A125.59 (14)N3B—C8B—C15B125.78 (14)
C9A—C8A—C15A119.75 (13)C9B—C8B—C15B118.47 (13)
C10A—C9A—C14A118.33 (14)C14B—C9B—C10B118.65 (13)
C10A—C9A—C8A121.20 (15)C14B—C9B—C8B120.69 (13)
C14A—C9A—C8A120.36 (13)C10B—C9B—C8B120.65 (14)
C9A—C10A—C11A120.53 (15)C11B—C10B—C9B120.98 (15)
C9A—C10A—H10B119.7C11B—C10B—H10A119.5
C11A—C10A—H10B119.7C9B—C10B—H10A119.5
C12A—C11A—C10A120.59 (15)C12B—C11B—C10B119.90 (15)
C12A—C11A—H11B119.7C12B—C11B—H11A120.0
C10A—C11A—H11B119.7C10B—C11B—H11A120.0
C11A—C12A—C13A119.33 (15)C11B—C12B—C13B119.84 (15)
C11A—C12A—H12B120.3C11B—C12B—H12A120.1
C13A—C12A—H12B120.3C13B—C12B—H12A120.1
C14A—C13A—C12A120.21 (16)C14B—C13B—C12B120.24 (16)
C14A—C13A—H13B119.9C14B—C13B—H13A119.9
C12A—C13A—H13B119.9C12B—C13B—H13A119.9
C13A—C14A—C9A120.99 (15)C13B—C14B—C9B120.37 (14)
C13A—C14A—H14B119.5C13B—C14B—H14A119.8
C9A—C14A—H14B119.5C9B—C14B—H14A119.8
C8A—C15A—H15D109.5C8B—C15B—H15A109.5
C8A—C15A—H15E109.5C8B—C15B—H15B109.5
H15D—C15A—H15E109.5H15A—C15B—H15B109.5
C8A—C15A—H15F109.5C8B—C15B—H15C109.5
H15D—C15A—H15F109.5H15A—C15B—H15C109.5
H15E—C15A—H15F109.5H15B—C15B—H15C109.5
C7A—N2A—N3A—C8A177.41 (14)C7B—N2B—N3B—C8B174.69 (14)
C7A—S1A—C1A—C2A178.25 (16)C7B—S1B—C1B—C2B177.91 (15)
C7A—S1A—C1A—C6A0.09 (12)C7B—S1B—C1B—C6B0.62 (11)
C6A—C1A—C2A—C3A0.6 (2)C6B—C1B—C2B—C3B0.4 (2)
S1A—C1A—C2A—C3A178.81 (13)S1B—C1B—C2B—C3B178.78 (12)
C1A—C2A—C3A—F1A179.81 (14)C1B—C2B—C3B—F1B179.57 (13)
C1A—C2A—C3A—C4A0.0 (2)C1B—C2B—C3B—C4B0.6 (2)
F1A—C3A—C4A—C5A178.95 (14)F1B—C3B—C4B—C5B179.14 (14)
C2A—C3A—C4A—C5A0.9 (3)C2B—C3B—C4B—C5B1.0 (2)
C3A—C4A—C5A—C6A1.0 (2)C3B—C4B—C5B—C6B0.4 (2)
C7A—N1A—C6A—C5A178.88 (15)C7B—N1B—C6B—C5B178.95 (14)
C7A—N1A—C6A—C1A0.23 (19)C7B—N1B—C6B—C1B0.19 (18)
C4A—C5A—C6A—N1A178.99 (14)C4B—C5B—C6B—N1B178.61 (14)
C4A—C5A—C6A—C1A0.4 (2)C4B—C5B—C6B—C1B0.5 (2)
C2A—C1A—C6A—N1A178.25 (14)C2B—C1B—C6B—N1B178.26 (13)
S1A—C1A—C6A—N1A0.20 (17)S1B—C1B—C6B—N1B0.39 (16)
C2A—C1A—C6A—C5A0.5 (2)C2B—C1B—C6B—C5B0.9 (2)
S1A—C1A—C6A—C5A178.93 (12)S1B—C1B—C6B—C5B179.59 (11)
C6A—N1A—C7A—N2A178.47 (14)C6B—N1B—C7B—N2B179.28 (14)
C6A—N1A—C7A—S1A0.16 (17)C6B—N1B—C7B—S1B0.72 (16)
N3A—N2A—C7A—N1A173.87 (14)N3B—N2B—C7B—N1B179.62 (14)
N3A—N2A—C7A—S1A7.51 (18)N3B—N2B—C7B—S1B1.86 (18)
C1A—S1A—C7A—N1A0.05 (13)C1B—S1B—C7B—N1B0.81 (13)
C1A—S1A—C7A—N2A178.65 (13)C1B—S1B—C7B—N2B179.43 (13)
N2A—N3A—C8A—C9A175.07 (13)N2B—N3B—C8B—C9B179.60 (13)
N2A—N3A—C8A—C15A2.9 (2)N2B—N3B—C8B—C15B0.8 (2)
N3A—C8A—C9A—C10A176.81 (14)N3B—C8B—C9B—C14B16.3 (2)
C15A—C8A—C9A—C10A5.1 (2)C15B—C8B—C9B—C14B164.85 (14)
N3A—C8A—C9A—C14A7.2 (2)N3B—C8B—C9B—C10B162.52 (14)
C15A—C8A—C9A—C14A170.95 (14)C15B—C8B—C9B—C10B16.3 (2)
C14A—C9A—C10A—C11A0.8 (2)C14B—C9B—C10B—C11B1.5 (2)
C8A—C9A—C10A—C11A175.31 (15)C8B—C9B—C10B—C11B177.34 (15)
C9A—C10A—C11A—C12A0.6 (3)C9B—C10B—C11B—C12B0.9 (2)
C10A—C11A—C12A—C13A1.4 (3)C10B—C11B—C12B—C13B0.0 (3)
C11A—C12A—C13A—C14A0.6 (3)C11B—C12B—C13B—C14B0.3 (2)
C12A—C13A—C14A—C9A0.8 (3)C12B—C13B—C14B—C9B0.2 (2)
C10A—C9A—C14A—C13A1.5 (2)C10B—C9B—C14B—C13B1.1 (2)
C8A—C9A—C14A—C13A174.61 (15)C8B—C9B—C14B—C13B177.69 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H1NA···N1Ai0.931.992.902 (2)165
N2B—H1NB···N1Bii0.792.142.9184 (18)168
C5B—H5BA···F1Biii0.952.513.310 (2)142
C12B—H12A···F1Aiv0.952.523.289 (2)138
C12A—H12B···F1Bv0.952.433.200 (2)138
C15B—H15A···N1Bii0.982.573.503 (2)160
Symmetry codes: (i) x+2, y, z+3/2; (ii) x+1, y, z+3/2; (iii) x, y+2, z1/2; (iv) x+2, y, z+5/2; (v) x+1, y+2, z+2.

Experimental details

Crystal data
Chemical formulaC15H12FN3S
Mr285.34
Crystal system, space groupMonoclinic, P2/c
Temperature (K)100
a, b, c (Å)28.312 (3), 7.2952 (7), 13.0626 (13)
β (°) 103.151 (2)
V3)2627.2 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.46 × 0.21 × 0.14
Data collection
DiffractometerBruker SMART APEXII DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.894, 0.965
No. of measured, independent and
observed [I > 2σ(I)] reflections
52781, 7411, 7049
Rint0.036
(sin θ/λ)max1)0.697
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.080, 1.06
No. of reflections7411
No. of parameters364
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N2A—H1NA···N1Ai0.931.992.902 (2)165
N2B—H1NB···N1Bii0.792.142.9184 (18)168
C5B—H5BA···F1Biii0.952.513.310 (2)142
C12B—H12A···F1Aiv0.952.523.289 (2)138
C12A—H12B···F1Bv0.952.433.200 (2)138
C15B—H15A···N1Bii0.982.573.503 (2)160
Symmetry codes: (i) x+2, y, z+3/2; (ii) x+1, y, z+3/2; (iii) x, y+2, z1/2; (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

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