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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 3| March 2013| Pages o392-o393

2-[5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-di­hydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole

aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 13 February 2013; accepted 13 February 2013; online 16 February 2013)

In the title compound, C25H20FN3S, two independent mol­ecules comprise the asymmetric unit, which differ in the relative orientation of the fluoro­benzene ring with respect to the pyrazole ring to which it is attached [dihedral angles = 89.39 (17) and 75.23 (16)° in the two mol­ecules]. Each pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. There are additional twists in the mol­ecules, e.g. between the five-membered rings [dihedral angles = 18.23 (16) and 17.84 (16)°] and between the thia­zole and attached phenyl ring [10.26 (16) and 20.87 (15)°]. Overall, each mol­ecule has a T-shape. In the crystal, mol­ecules are connected into a three-dimensional architecture by weak C—H⋯π inter­actions.

Related literature

For the biological activity of pyrazolin-1-yl­thia­zoles, see: Abdel-Wahab et al. (2009[Abdel-Wahab, B. F., Abdel-Aziz, H. A. & Ahmed, E. M. (2009). Eur. J. Med. Chem. 44, 2632-2635.], 2012[Abdel-Wahab, B. F., Abdel-Latif, E., Mohamed, H. A. & Awad, G. E. A. (2012). Eur. J. Med. Chem. 52, 263-268.]); Chimenti et al. (2010[Chimenti, F., Carradori, S., Secci, D., Bolasco, A., Bizzarri, B., Chimenti, P., Granese, A., Yáñez, M. & Orallo, F. (2010). Eur. J. Med. Chem. 45, 800-804.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C25H20FN3S

  • Mr = 413.50

  • Monoclinic, P c

  • a = 5.7563 (3) Å

  • b = 24.1214 (12) Å

  • c = 15.1827 (8) Å

  • β = 90.948 (5)°

  • V = 2107.83 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.18 mm−1

  • T = 295 K

  • 0.40 × 0.30 × 0.20 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.837, Tmax = 1.000

  • 22651 measured reflections

  • 9054 independent reflections

  • 5841 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.117

  • S = 0.99

  • 9054 reflections

  • 543 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.16 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4165 Friedel pairs

  • Flack parameter: −0.06 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C26–C31, C45–C50, S2,N4,C32–C34 and C1–C6 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C15—H15⋯Cg1 0.93 2.75 3.537 (3) 143
C19—H19ACg2i 0.96 2.94 3.596 (4) 127
C35—H35⋯Cg3ii 0.98 2.94 3.843 (3) 153
C42—H42⋯Cg4iii 0.93 2.86 3.567 (3) 134
Symmetry codes: (i) [x, -y, z+{\script{1\over 2}}]; (ii) x-1, y, z; (iii) [x, -y+1, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), QMol (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The title compound (I) was investigated in relation to the established biological activities exhibited by pyrazolin-1-ylthiazoles (Abdel-Wahab et al., 2012; Abdel-Wahab et al., 2009; Chimenti et al., 2010).

Two independent molecules comprise the crystallographic asymmetric unit of (I), Fig. 1. As judged from the overlay diagram, Fig. 2, the central residues are super-imposable with the major difference relating to the relative orientations of the fluorobenzene rings with the dihedral angle formed with the least-squares plane through the pyrazolyl ring being 89.39 (17)° for the S1-containing molecule and 75.23 (16)° for the second molecule. Each pyrazolyl ring adopts an envelope conformation with the methine-C atom, i.e. C10 and C35, being the flap atom in each case. With the exception of the near perpendicular relationship between the pyrazolyl and fluorobenzene rings, the remaining components of the molecule exhibit relatively small twists as indicated by the dihedral angles formed between the five-membered rings [18.23 (16); 17.84 (16)°], the thiazolyl and attached phenyl ring [10.26 (16); 20.87 (15)°], and between the pyrazolyl and appended tolyl ring [2.37 (16); 1.96 (16)°]. Overall, the molecule has the shape of the letter T and resembles the structure of a literature precedent (Fun et al., 2011).

The crystal packing is dominated by C—H···π interactions that lead to a three-dimensional architecture, Fig. 3 and Table 1.

Related literature top

For the biological activity of pyrazolin-1-ylthiazoles, see: Abdel-Wahab et al. (2009, 2012); Chimenti et al. (2010). For a related structure, see: Fun et al. (2011).

Experimental top

A mixture of 5-(4-fluorophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (0.31 g, 0.001 M) and 2-bromo-1-phenylethanone (0.2 g, 0.001 M) in anhydrous ethanol (30 ml) was heated under reflux for about 4 h. The resultant solid was filtered and dried. Re-crystallization was by slow evaporation of a DMF solution of (I) which yielded colourless crystals in 59% yield. M.pt. 418–420 K.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2–1.5Uequiv(C).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
[Figure 2] Fig. 2. Overlay diagram of the two independent molecules in (I) with the S1-containing molecule illustrated in red. The molecules are overlaid so that the thiazolyl rings are superimposed.
[Figure 3] Fig. 3. A view of the crystal packing in projection down the a axis. The C—H···π interactions are shown as purple dashed lines.
2-[5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thiazole top
Crystal data top
C25H20FN3SF(000) = 864
Mr = 413.50Dx = 1.303 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 5001 reflections
a = 5.7563 (3) Åθ = 2.9–27.5°
b = 24.1214 (12) ŵ = 0.18 mm1
c = 15.1827 (8) ÅT = 295 K
β = 90.948 (5)°Prism, yellow
V = 2107.83 (19) Å30.40 × 0.30 × 0.20 mm
Z = 4
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
9054 independent reflections
Radiation source: SuperNova (Mo) X-ray Source5841 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.042
Detector resolution: 10.4041 pixels mm-1θmax = 27.6°, θmin = 2.9°
ω scanh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
k = 3131
Tmin = 0.837, Tmax = 1.000l = 1919
22651 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0492P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
9054 reflectionsΔρmax = 0.14 e Å3
543 parametersΔρmin = 0.16 e Å3
2 restraintsAbsolute structure: Flack (1983), 4165 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (6)
Crystal data top
C25H20FN3SV = 2107.83 (19) Å3
Mr = 413.50Z = 4
Monoclinic, PcMo Kα radiation
a = 5.7563 (3) ŵ = 0.18 mm1
b = 24.1214 (12) ÅT = 295 K
c = 15.1827 (8) Å0.40 × 0.30 × 0.20 mm
β = 90.948 (5)°
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
9054 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
5841 reflections with I > 2σ(I)
Tmin = 0.837, Tmax = 1.000Rint = 0.042
22651 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.117Δρmax = 0.14 e Å3
S = 0.99Δρmin = 0.16 e Å3
9054 reflectionsAbsolute structure: Flack (1983), 4165 Friedel pairs
543 parametersAbsolute structure parameter: 0.06 (6)
2 restraints
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
S10.49969 (14)0.29737 (3)0.50008 (6)0.0662 (2)
S21.01138 (13)0.25628 (3)0.36822 (6)0.0666 (2)
F10.0507 (5)0.34215 (9)0.99078 (17)0.1149 (8)
F20.5094 (5)0.12749 (9)0.12101 (16)0.1042 (7)
N10.1354 (4)0.32997 (10)0.58332 (16)0.0579 (6)
N20.2741 (4)0.24238 (11)0.62782 (17)0.0638 (7)
N30.4085 (4)0.19780 (11)0.60017 (17)0.0621 (7)
N40.8192 (4)0.17483 (10)0.28401 (16)0.0585 (6)
N50.6904 (4)0.26272 (10)0.23727 (18)0.0635 (7)
N60.6916 (4)0.31858 (10)0.26139 (16)0.0590 (7)
C10.0526 (5)0.42283 (12)0.52259 (19)0.0571 (8)
C20.1262 (6)0.46954 (15)0.4761 (2)0.0740 (9)
H2A0.26310.46800.44450.089*
C30.0020 (7)0.51781 (16)0.4767 (3)0.0822 (11)
H30.05190.54890.44700.099*
C40.2069 (7)0.52053 (16)0.5204 (3)0.0835 (11)
H40.29470.55290.51920.100*
C50.2824 (6)0.47491 (16)0.5663 (2)0.0758 (10)
H50.42140.47660.59650.091*
C60.1532 (6)0.42654 (14)0.5678 (2)0.0653 (8)
H60.20550.39620.59950.078*
C70.1944 (5)0.37188 (12)0.52465 (19)0.0554 (7)
C80.3820 (6)0.36115 (13)0.4756 (2)0.0643 (8)
H80.44060.38530.43360.077*
C90.2832 (5)0.28972 (13)0.57623 (19)0.0559 (7)
C100.0630 (5)0.22505 (13)0.6747 (2)0.0606 (8)
H100.07350.22970.63600.073*
C110.1131 (6)0.16282 (13)0.6878 (2)0.0664 (9)
H11A0.14530.15440.74930.080*
H11B0.01680.14040.66730.080*
C120.3231 (5)0.15310 (13)0.6329 (2)0.0569 (7)
C130.4368 (5)0.09940 (13)0.61754 (19)0.0566 (7)
C140.6347 (5)0.09546 (14)0.5673 (2)0.0640 (8)
H140.69260.12700.54020.077*
C150.7465 (6)0.04580 (14)0.5568 (2)0.0671 (9)
H150.88000.04450.52320.081*
C160.6653 (5)0.00304 (13)0.5954 (2)0.0618 (8)
C170.4650 (6)0.00095 (14)0.6425 (2)0.0659 (8)
H170.40400.03090.66770.079*
C180.3500 (6)0.05102 (14)0.6539 (2)0.0652 (8)
H180.21400.05210.68610.078*
C190.7985 (6)0.05603 (14)0.5865 (3)0.0827 (11)
H19A0.71800.08530.61610.124*
H19B0.95060.05160.61250.124*
H19C0.81230.06510.52530.124*
C200.0305 (5)0.25749 (12)0.7580 (2)0.0542 (7)
C210.1996 (5)0.25682 (13)0.8234 (2)0.0637 (8)
H210.33450.23650.81460.076*
C220.1749 (7)0.28550 (14)0.9016 (2)0.0733 (9)
H220.29020.28440.94520.088*
C230.0195 (7)0.31483 (13)0.9126 (2)0.0731 (10)
C240.1901 (7)0.31738 (15)0.8503 (3)0.0816 (11)
H240.32360.33800.86030.098*
C250.1649 (6)0.28920 (14)0.7719 (3)0.0709 (9)
H250.28000.29160.72840.085*
C261.0106 (5)0.09110 (13)0.34701 (18)0.0561 (7)
C271.2113 (6)0.06737 (16)0.3842 (2)0.0696 (9)
H271.33080.09010.40480.084*
C281.2335 (6)0.01085 (17)0.3907 (2)0.0775 (10)
H281.36760.00430.41570.093*
C291.0595 (6)0.02337 (15)0.3605 (2)0.0737 (10)
H291.07580.06170.36450.088*
C300.8601 (6)0.00060 (15)0.3242 (2)0.0731 (9)
H300.74050.02360.30450.088*
C310.8373 (6)0.05605 (13)0.3171 (2)0.0643 (8)
H310.70290.07090.29170.077*
C320.9822 (5)0.15215 (13)0.34277 (19)0.0551 (7)
C331.0981 (6)0.18976 (14)0.3925 (2)0.0644 (8)
H331.21100.18080.43470.077*
C340.8228 (5)0.22829 (13)0.2909 (2)0.0550 (7)
C350.4651 (5)0.24534 (12)0.1964 (2)0.0559 (8)
H350.37400.22460.23920.067*
C360.3531 (5)0.30230 (12)0.1797 (2)0.0619 (8)
H36A0.34830.31090.11730.074*
H36B0.19640.30340.20210.074*
C370.5083 (5)0.34182 (12)0.22889 (19)0.0544 (7)
C380.4623 (5)0.40098 (12)0.23963 (19)0.0531 (7)
C390.6205 (5)0.43590 (13)0.2823 (2)0.0608 (8)
H390.75940.42160.30460.073*
C400.5724 (6)0.49193 (13)0.2918 (2)0.0673 (9)
H400.67970.51460.32070.081*
C410.3681 (6)0.51480 (13)0.2591 (2)0.0619 (8)
C420.2136 (6)0.48056 (13)0.2167 (2)0.0646 (8)
H420.07600.49520.19380.077*
C430.2585 (5)0.42450 (12)0.2075 (2)0.0629 (8)
H430.14930.40210.17900.075*
C440.3189 (8)0.57637 (13)0.2676 (3)0.0901 (12)
H44A0.35060.58800.32700.135*
H44B0.15880.58340.25290.135*
H44C0.41630.59660.22810.135*
C450.4915 (5)0.21170 (11)0.1141 (2)0.0520 (7)
C460.6698 (5)0.21963 (12)0.0566 (2)0.0607 (8)
H460.78720.24470.07110.073*
C470.6789 (6)0.19115 (13)0.0227 (2)0.0671 (8)
H470.80140.19630.06100.081*
C480.5029 (7)0.15541 (13)0.0426 (2)0.0689 (9)
C490.3243 (7)0.14560 (14)0.0122 (3)0.0758 (10)
H490.20830.12040.00310.091*
C500.3179 (6)0.17378 (13)0.0911 (3)0.0696 (9)
H500.19640.16740.12940.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0668 (5)0.0716 (5)0.0607 (5)0.0069 (4)0.0122 (4)0.0014 (4)
S20.0692 (5)0.0773 (5)0.0529 (5)0.0069 (4)0.0124 (4)0.0081 (4)
F10.177 (2)0.0779 (13)0.0908 (16)0.0016 (15)0.0292 (17)0.0204 (13)
F20.1388 (19)0.0879 (13)0.0854 (15)0.0013 (14)0.0106 (15)0.0298 (13)
N10.0642 (15)0.0663 (15)0.0432 (14)0.0055 (13)0.0048 (12)0.0038 (12)
N20.0670 (16)0.0699 (16)0.0547 (16)0.0006 (13)0.0104 (13)0.0083 (13)
N30.0647 (16)0.0700 (17)0.0518 (16)0.0040 (13)0.0053 (13)0.0062 (13)
N40.0555 (14)0.0685 (16)0.0512 (15)0.0116 (12)0.0105 (12)0.0020 (13)
N50.0650 (15)0.0591 (15)0.0655 (17)0.0098 (12)0.0209 (13)0.0019 (13)
N60.0581 (14)0.0603 (14)0.0582 (16)0.0021 (12)0.0104 (13)0.0035 (12)
C10.0609 (18)0.0634 (18)0.0467 (17)0.0098 (15)0.0093 (14)0.0040 (14)
C20.072 (2)0.083 (2)0.067 (2)0.0057 (19)0.0038 (18)0.0146 (18)
C30.086 (3)0.077 (2)0.084 (3)0.007 (2)0.001 (2)0.021 (2)
C40.095 (3)0.075 (2)0.080 (3)0.012 (2)0.013 (2)0.003 (2)
C50.065 (2)0.097 (3)0.065 (2)0.001 (2)0.0001 (17)0.010 (2)
C60.067 (2)0.074 (2)0.0554 (19)0.0061 (17)0.0055 (16)0.0052 (16)
C70.0610 (18)0.0633 (18)0.0418 (16)0.0145 (15)0.0016 (14)0.0017 (14)
C80.071 (2)0.0666 (18)0.0557 (19)0.0123 (16)0.0138 (17)0.0013 (16)
C90.0605 (17)0.0673 (18)0.0400 (16)0.0059 (15)0.0001 (14)0.0010 (14)
C100.0497 (16)0.077 (2)0.0553 (19)0.0016 (15)0.0042 (15)0.0081 (16)
C110.066 (2)0.070 (2)0.063 (2)0.0097 (16)0.0016 (17)0.0006 (16)
C120.0578 (17)0.0697 (19)0.0431 (16)0.0068 (15)0.0077 (14)0.0023 (15)
C130.0549 (17)0.0694 (19)0.0454 (17)0.0034 (15)0.0060 (14)0.0019 (15)
C140.067 (2)0.070 (2)0.0549 (19)0.0090 (16)0.0011 (16)0.0005 (15)
C150.0645 (19)0.083 (2)0.0536 (19)0.0008 (18)0.0027 (16)0.0129 (18)
C160.066 (2)0.070 (2)0.0495 (18)0.0079 (16)0.0076 (16)0.0106 (16)
C170.072 (2)0.0660 (19)0.060 (2)0.0098 (17)0.0073 (17)0.0031 (16)
C180.0619 (18)0.078 (2)0.055 (2)0.0063 (17)0.0025 (15)0.0022 (17)
C190.093 (3)0.076 (2)0.079 (3)0.002 (2)0.003 (2)0.018 (2)
C200.0501 (16)0.0601 (16)0.0524 (18)0.0029 (14)0.0026 (14)0.0095 (14)
C210.0591 (18)0.0691 (19)0.063 (2)0.0061 (15)0.0053 (16)0.0031 (16)
C220.086 (2)0.074 (2)0.061 (2)0.0015 (19)0.0048 (19)0.0029 (18)
C230.101 (3)0.0535 (18)0.065 (2)0.0041 (19)0.018 (2)0.0044 (17)
C240.079 (2)0.072 (2)0.094 (3)0.0243 (19)0.025 (2)0.012 (2)
C250.064 (2)0.076 (2)0.072 (2)0.0103 (17)0.0082 (18)0.0179 (19)
C260.0527 (17)0.0735 (19)0.0421 (16)0.0104 (15)0.0006 (13)0.0056 (14)
C270.0572 (18)0.086 (2)0.065 (2)0.0125 (16)0.0054 (16)0.0035 (17)
C280.072 (2)0.090 (3)0.070 (2)0.032 (2)0.0053 (18)0.011 (2)
C290.089 (2)0.075 (2)0.057 (2)0.021 (2)0.0019 (19)0.0079 (18)
C300.082 (2)0.074 (2)0.063 (2)0.0094 (18)0.0098 (18)0.0033 (17)
C310.0614 (18)0.075 (2)0.056 (2)0.0131 (17)0.0110 (15)0.0077 (16)
C320.0491 (16)0.0733 (19)0.0427 (16)0.0079 (14)0.0031 (13)0.0041 (15)
C330.0628 (18)0.084 (2)0.0461 (18)0.0082 (16)0.0112 (15)0.0038 (16)
C340.0531 (16)0.0656 (18)0.0464 (17)0.0087 (15)0.0025 (13)0.0003 (15)
C350.0519 (16)0.0605 (17)0.0549 (18)0.0004 (13)0.0085 (14)0.0037 (14)
C360.0619 (18)0.0592 (18)0.064 (2)0.0058 (15)0.0104 (16)0.0040 (15)
C370.0552 (17)0.0613 (17)0.0465 (17)0.0025 (14)0.0024 (14)0.0037 (14)
C380.0543 (16)0.0603 (17)0.0447 (16)0.0033 (14)0.0028 (13)0.0045 (14)
C390.0578 (18)0.0704 (19)0.0540 (18)0.0023 (15)0.0047 (15)0.0073 (16)
C400.074 (2)0.067 (2)0.061 (2)0.0159 (17)0.0003 (18)0.0023 (17)
C410.073 (2)0.0603 (18)0.0528 (18)0.0029 (16)0.0070 (16)0.0015 (15)
C420.0629 (19)0.0662 (19)0.065 (2)0.0081 (16)0.0029 (16)0.0008 (17)
C430.0617 (18)0.0603 (18)0.066 (2)0.0000 (15)0.0092 (16)0.0009 (16)
C440.116 (3)0.062 (2)0.092 (3)0.003 (2)0.004 (2)0.004 (2)
C450.0508 (16)0.0504 (15)0.0544 (18)0.0006 (13)0.0078 (15)0.0096 (13)
C460.0610 (18)0.0540 (16)0.067 (2)0.0112 (14)0.0064 (17)0.0056 (16)
C470.072 (2)0.0654 (18)0.064 (2)0.0014 (17)0.0083 (17)0.0076 (17)
C480.086 (2)0.0556 (18)0.065 (2)0.0055 (17)0.012 (2)0.0073 (16)
C490.078 (2)0.068 (2)0.081 (3)0.0147 (18)0.013 (2)0.0119 (19)
C500.0591 (18)0.0695 (19)0.080 (2)0.0128 (16)0.0003 (17)0.0046 (19)
Geometric parameters (Å, º) top
S1—C81.719 (3)C20—C251.379 (4)
S1—C91.724 (3)C21—C221.384 (5)
S2—C331.719 (3)C21—H210.9300
S2—C341.723 (3)C22—C231.337 (5)
F1—C231.371 (4)C22—H220.9300
F2—C481.369 (4)C23—C241.353 (5)
N1—C91.297 (4)C24—C251.381 (5)
N1—C71.393 (4)C24—H240.9300
N2—C91.386 (4)C25—H250.9300
N2—N31.393 (4)C26—C311.379 (4)
N2—C101.479 (4)C26—C271.400 (4)
N3—C121.288 (4)C26—C321.483 (4)
N4—C341.294 (4)C27—C281.373 (5)
N4—C321.396 (3)C27—H270.9300
N5—C341.384 (3)C28—C291.370 (5)
N5—N61.396 (3)C28—H280.9300
N5—C351.489 (3)C29—C301.379 (5)
N6—C371.286 (3)C29—H290.9300
C1—C61.381 (4)C30—C311.377 (5)
C1—C21.399 (4)C30—H300.9300
C1—C71.476 (4)C31—H310.9300
C2—C31.379 (5)C32—C331.349 (4)
C2—H2A0.9300C33—H330.9300
C3—C41.364 (5)C35—C451.500 (4)
C3—H30.9300C35—C361.537 (4)
C4—C51.377 (5)C35—H350.9800
C4—H40.9300C36—C371.498 (4)
C5—C61.384 (5)C36—H36A0.9700
C5—H50.9300C36—H36B0.9700
C6—H60.9300C37—C381.461 (4)
C7—C81.347 (4)C38—C431.385 (4)
C8—H80.9300C38—C391.392 (4)
C10—C201.502 (4)C39—C401.388 (4)
C10—C111.541 (4)C39—H390.9300
C10—H100.9800C40—C411.384 (4)
C11—C121.498 (5)C40—H400.9300
C11—H11A0.9700C41—C421.366 (4)
C11—H11B0.9700C41—C441.518 (4)
C12—C131.472 (4)C42—C431.384 (4)
C13—C141.384 (4)C42—H420.9300
C13—C181.388 (4)C43—H430.9300
C14—C151.371 (4)C44—H44A0.9600
C14—H140.9300C44—H44B0.9600
C15—C161.400 (5)C44—H44C0.9600
C15—H150.9300C45—C461.372 (4)
C16—C171.370 (4)C45—C501.395 (4)
C16—C191.498 (5)C46—C471.388 (5)
C17—C181.390 (5)C46—H460.9300
C17—H170.9300C47—C481.360 (5)
C18—H180.9300C47—H470.9300
C19—H19A0.9600C48—C491.354 (5)
C19—H19B0.9600C49—C501.378 (5)
C19—H19C0.9600C49—H490.9300
C20—C211.379 (4)C50—H500.9300
C8—S1—C987.38 (16)C23—C24—C25119.7 (3)
C33—S2—C3487.58 (14)C23—C24—H24120.2
C9—N1—C7108.8 (3)C25—C24—H24120.2
C9—N2—N3116.0 (3)C20—C25—C24120.2 (3)
C9—N2—C10123.0 (2)C20—C25—H25119.9
N3—N2—C10113.1 (2)C24—C25—H25119.9
C12—N3—N2108.2 (3)C31—C26—C27118.0 (3)
C34—N4—C32109.2 (2)C31—C26—C32121.1 (2)
C34—N5—N6115.1 (2)C27—C26—C32120.9 (3)
C34—N5—C35123.0 (2)C28—C27—C26120.7 (3)
N6—N5—C35112.4 (2)C28—C27—H27119.7
C37—N6—N5108.6 (2)C26—C27—H27119.7
C6—C1—C2117.9 (3)C29—C28—C27120.5 (3)
C6—C1—C7121.5 (3)C29—C28—H28119.7
C2—C1—C7120.6 (3)C27—C28—H28119.7
C3—C2—C1120.7 (4)C28—C29—C30119.5 (3)
C3—C2—H2A119.6C28—C29—H29120.2
C1—C2—H2A119.6C30—C29—H29120.2
C4—C3—C2120.7 (4)C31—C30—C29120.3 (3)
C4—C3—H3119.6C31—C30—H30119.9
C2—C3—H3119.6C29—C30—H30119.9
C3—C4—C5119.4 (4)C30—C31—C26121.0 (3)
C3—C4—H4120.3C30—C31—H31119.5
C5—C4—H4120.3C26—C31—H31119.5
C4—C5—C6120.5 (4)C33—C32—N4114.5 (3)
C4—C5—H5119.7C33—C32—C26126.2 (2)
C6—C5—H5119.7N4—C32—C26119.3 (3)
C5—C6—C1120.8 (3)C32—C33—S2111.6 (2)
C5—C6—H6119.6C32—C33—H33124.2
C1—C6—H6119.6S2—C33—H33124.2
C8—C7—N1114.9 (3)N4—C34—N5122.8 (3)
C8—C7—C1126.6 (3)N4—C34—S2117.1 (2)
N1—C7—C1118.5 (3)N5—C34—S2120.0 (2)
C7—C8—S1111.6 (2)N5—C35—C45113.6 (3)
C7—C8—H8124.2N5—C35—C36100.2 (2)
S1—C8—H8124.2C45—C35—C36113.2 (2)
N1—C9—N2122.6 (3)N5—C35—H35109.8
N1—C9—S1117.3 (2)C45—C35—H35109.8
N2—C9—S1120.1 (2)C36—C35—H35109.8
N2—C10—C20111.9 (2)C37—C36—C35104.0 (2)
N2—C10—C11100.6 (2)C37—C36—H36A111.0
C20—C10—C11115.1 (3)C35—C36—H36A111.0
N2—C10—H10109.6C37—C36—H36B111.0
C20—C10—H10109.6C35—C36—H36B111.0
C11—C10—H10109.6H36A—C36—H36B109.0
C12—C11—C10103.4 (3)N6—C37—C38122.2 (3)
C12—C11—H11A111.1N6—C37—C36113.1 (3)
C10—C11—H11A111.1C38—C37—C36124.7 (2)
C12—C11—H11B111.1C43—C38—C39117.4 (3)
C10—C11—H11B111.1C43—C38—C37121.0 (3)
H11A—C11—H11B109.0C39—C38—C37121.6 (3)
N3—C12—C13120.1 (3)C40—C39—C38120.5 (3)
N3—C12—C11113.6 (3)C40—C39—H39119.7
C13—C12—C11126.2 (3)C38—C39—H39119.7
C14—C13—C18117.8 (3)C41—C40—C39121.4 (3)
C14—C13—C12121.3 (3)C41—C40—H40119.3
C18—C13—C12120.8 (3)C39—C40—H40119.3
C15—C14—C13121.1 (3)C42—C41—C40118.1 (3)
C15—C14—H14119.5C42—C41—C44120.7 (3)
C13—C14—H14119.5C40—C41—C44121.2 (3)
C14—C15—C16121.8 (3)C41—C42—C43121.1 (3)
C14—C15—H15119.1C41—C42—H42119.4
C16—C15—H15119.1C43—C42—H42119.4
C17—C16—C15116.7 (3)C38—C43—C42121.5 (3)
C17—C16—C19122.9 (3)C38—C43—H43119.2
C15—C16—C19120.4 (3)C42—C43—H43119.2
C16—C17—C18122.2 (3)C41—C44—H44A109.5
C16—C17—H17118.9C41—C44—H44B109.5
C18—C17—H17118.9H44A—C44—H44B109.5
C17—C18—C13120.4 (3)C41—C44—H44C109.5
C17—C18—H18119.8H44A—C44—H44C109.5
C13—C18—H18119.8H44B—C44—H44C109.5
C16—C19—H19A109.5C46—C45—C50118.2 (3)
C16—C19—H19B109.5C46—C45—C35122.8 (3)
H19A—C19—H19B109.5C50—C45—C35118.8 (3)
C16—C19—H19C109.5C45—C46—C47121.5 (3)
H19A—C19—H19C109.5C45—C46—H46119.3
H19B—C19—H19C109.5C47—C46—H46119.3
C21—C20—C25117.7 (3)C48—C47—C46117.9 (3)
C21—C20—C10120.2 (3)C48—C47—H47121.1
C25—C20—C10122.1 (3)C46—C47—H47121.1
C20—C21—C22122.0 (3)C49—C48—C47123.0 (3)
C20—C21—H21119.0C49—C48—F2118.7 (3)
C22—C21—H21119.0C47—C48—F2118.3 (4)
C23—C22—C21118.0 (3)C48—C49—C50118.6 (3)
C23—C22—H22121.0C48—C49—H49120.7
C21—C22—H22121.0C50—C49—H49120.7
C22—C23—C24122.4 (3)C49—C50—C45120.8 (4)
C22—C23—F1119.0 (4)C49—C50—H50119.6
C24—C23—F1118.6 (4)C45—C50—H50119.6
C9—N2—N3—C12157.5 (2)C10—C20—C25—C24178.5 (3)
C10—N2—N3—C127.5 (3)C23—C24—C25—C201.6 (5)
C34—N5—N6—C37157.5 (3)C31—C26—C27—C280.2 (5)
C35—N5—N6—C3710.0 (3)C32—C26—C27—C28177.8 (3)
C6—C1—C2—C30.8 (5)C26—C27—C28—C290.2 (5)
C7—C1—C2—C3177.7 (3)C27—C28—C29—C300.6 (6)
C1—C2—C3—C42.0 (5)C28—C29—C30—C311.0 (5)
C2—C3—C4—C51.8 (6)C29—C30—C31—C261.0 (5)
C3—C4—C5—C60.5 (5)C27—C26—C31—C300.5 (5)
C4—C5—C6—C10.7 (5)C32—C26—C31—C30177.4 (3)
C2—C1—C6—C50.5 (4)C34—N4—C32—C331.2 (4)
C7—C1—C6—C5179.0 (3)C34—N4—C32—C26180.0 (3)
C9—N1—C7—C80.6 (3)C31—C26—C32—C33157.8 (3)
C9—N1—C7—C1178.6 (2)C27—C26—C32—C3320.1 (5)
C6—C1—C7—C8171.7 (3)C31—C26—C32—N420.9 (4)
C2—C1—C7—C89.8 (4)C27—C26—C32—N4161.2 (3)
C6—C1—C7—N19.2 (4)N4—C32—C33—S20.4 (4)
C2—C1—C7—N1169.3 (3)C26—C32—C33—S2179.1 (3)
N1—C7—C8—S10.3 (3)C34—S2—C33—C320.3 (3)
C1—C7—C8—S1178.8 (2)C32—N4—C34—N5175.9 (3)
C9—S1—C8—C70.0 (2)C32—N4—C34—S21.5 (4)
C7—N1—C9—N2178.3 (2)N6—N5—C34—N4171.7 (3)
C7—N1—C9—S10.7 (3)C35—N5—C34—N428.0 (5)
N3—N2—C9—N1166.1 (3)N6—N5—C34—S210.9 (4)
C10—N2—C9—N119.3 (4)C35—N5—C34—S2154.7 (2)
N3—N2—C9—S115.0 (3)C33—S2—C34—N41.1 (3)
C10—N2—C9—S1161.7 (2)C33—S2—C34—N5176.4 (3)
C8—S1—C9—N10.4 (2)C34—N5—C35—C4581.5 (4)
C8—S1—C9—N2178.6 (2)N6—N5—C35—C45133.9 (3)
C9—N2—C10—C2078.9 (3)C34—N5—C35—C36157.5 (3)
N3—N2—C10—C20133.5 (2)N6—N5—C35—C3612.9 (3)
C9—N2—C10—C11158.3 (3)N5—C35—C36—C3710.7 (3)
N3—N2—C10—C1110.7 (3)C45—C35—C36—C37132.0 (3)
N2—C10—C11—C129.4 (3)N5—N6—C37—C38177.7 (3)
C20—C10—C11—C12129.9 (3)N5—N6—C37—C361.9 (4)
N2—N3—C12—C13177.4 (2)C35—C36—C37—N66.2 (4)
N2—N3—C12—C110.4 (3)C35—C36—C37—C38174.2 (3)
C10—C11—C12—N36.2 (3)N6—C37—C38—C43177.0 (3)
C10—C11—C12—C13176.1 (3)C36—C37—C38—C433.4 (5)
N3—C12—C13—C140.7 (4)N6—C37—C38—C393.1 (5)
C11—C12—C13—C14178.2 (3)C36—C37—C38—C39176.5 (3)
N3—C12—C13—C18178.6 (3)C43—C38—C39—C400.2 (5)
C11—C12—C13—C181.1 (4)C37—C38—C39—C40179.9 (3)
C18—C13—C14—C152.6 (4)C38—C39—C40—C410.3 (5)
C12—C13—C14—C15176.7 (3)C39—C40—C41—C420.1 (5)
C13—C14—C15—C160.6 (4)C39—C40—C41—C44178.4 (3)
C14—C15—C16—C171.5 (4)C40—C41—C42—C430.6 (5)
C14—C15—C16—C19176.8 (3)C44—C41—C42—C43179.0 (3)
C15—C16—C17—C181.7 (4)C39—C38—C43—C420.4 (5)
C19—C16—C17—C18176.6 (3)C37—C38—C43—C42179.6 (3)
C16—C17—C18—C130.3 (4)C41—C42—C43—C380.8 (5)
C14—C13—C18—C172.4 (4)N5—C35—C45—C4632.9 (4)
C12—C13—C18—C17176.9 (3)C36—C35—C45—C4680.5 (3)
N2—C10—C20—C2158.9 (4)N5—C35—C45—C50152.4 (3)
C11—C10—C20—C2155.1 (4)C36—C35—C45—C5094.2 (3)
N2—C10—C20—C25120.4 (3)C50—C45—C46—C470.3 (4)
C11—C10—C20—C25125.6 (3)C35—C45—C46—C47174.5 (3)
C25—C20—C21—C221.7 (5)C45—C46—C47—C480.9 (5)
C10—C20—C21—C22179.1 (3)C46—C47—C48—C491.7 (5)
C20—C21—C22—C230.5 (5)C46—C47—C48—F2179.4 (3)
C21—C22—C23—C240.2 (6)C47—C48—C49—C501.2 (5)
C21—C22—C23—F1178.0 (3)F2—C48—C49—C50179.9 (3)
C22—C23—C24—C250.4 (6)C48—C49—C50—C450.1 (5)
F1—C23—C24—C25178.6 (3)C46—C45—C50—C490.8 (4)
C21—C20—C25—C242.2 (5)C35—C45—C50—C49174.2 (3)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C26–C31, C45–C50, S2,N4,C32–C34 and C1–C6 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C15—H15···Cg10.932.753.537 (3)143
C19—H19A···Cg2i0.962.943.596 (4)127
C35—H35···Cg3ii0.982.943.843 (3)153
C42—H42···Cg4iii0.932.863.567 (3)134
Symmetry codes: (i) x, y, z+1/2; (ii) x1, y, z; (iii) x, y+1, z1/2.

Experimental details

Crystal data
Chemical formulaC25H20FN3S
Mr413.50
Crystal system, space groupMonoclinic, Pc
Temperature (K)295
a, b, c (Å)5.7563 (3), 24.1214 (12), 15.1827 (8)
β (°) 90.948 (5)
V3)2107.83 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2011)
Tmin, Tmax0.837, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
22651, 9054, 5841
Rint0.042
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.117, 0.99
No. of reflections9054
No. of parameters543
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.16
Absolute structureFlack (1983), 4165 Friedel pairs
Absolute structure parameter0.06 (6)

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C26–C31, C45–C50, S2,N4,C32–C34 and C1–C6 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C15—H15···Cg10.932.753.537 (3)143
C19—H19A···Cg2i0.962.943.596 (4)127
C35—H35···Cg3ii0.982.943.843 (3)153
C42—H42···Cg4iii0.932.863.567 (3)134
Symmetry codes: (i) x, y, z+1/2; (ii) x1, y, z; (iii) x, y+1, z1/2.
 

Footnotes

Additional correspondence author, e-mail: bakrfatehy@yahoo.com.

Acknowledgements

We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

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Volume 69| Part 3| March 2013| Pages o392-o393
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