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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3,5-Bis(4-fluoro­phen­yl)-1-phenyl-4,5-di­hydro-1H-pyrazole

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
*Correspondence e-mail: jjasinski@keene.edu

(Received 25 June 2010; accepted 1 July 2010; online 7 July 2010)

In the title compound, C21H16F2N2, the dihedral angle between the fluoro­phenyl groups is 66.34 (8)°, and the dihedral angle between the envelope-configured pyrazole group (N/N/C/C/C) and the benzene ring is 11.50 (9)°. The dihedral angles between the benzene and the two fluoro-substituted phenyl groups are 77.7 (6) and 16.7 (5)°. Weak C—H⋯π interactions contribute to the stability of the crystal structure.

Related literature

For background to the chemistry and biological activity of pyrazolines, see: Amir et al. (2008[Amir, M., Kumar, H. & Khan, S. A. (2008). Bioorg. Med. Chem. Lett. 18, 918-922.]); Bhaskarreddy et al. (1997[Bhaskarreddy, D., Chandrasekhar, B. N., Padmavathi, V. & Sumathi, R. P. (1997). Synthesis, 3, 491-494.]); Fustero et al. (2009[Fustero, S., Fuentes, A. S. & Sanz-Cervera, J. F. (2009). Org. Prep. Proc. Int. 41, 253-290.]); Hes et al. (1978[Hes, R. V., Wellinga, K. & Grosscurt, A. C. (1978). J. Agric. Food Chem. 26, 915-918.]); Klimova et al. (1999[Klimova, E. I., Marcos, M., Klimova, T. B., Cecilio, A. T., Ruben, A. T. & Lena, R. R. (1999). J. Organomet. Chem. 585, 106-111.]); Regaila et al. (1979[Regaila, H. A., El-Bayonk, A. K. & Hammad, M. (1979). Egypt. J. Chem. 20, 197-202.]); Sarojini et al. (2010[Sarojini, B. K., Vidyagayatri, M., Darshanraj, C. G., Bharath, B. R. & Manjunatha, H. (2010). Lett. Drug Des. Discovery, 7, 214-224.]); Wiley et al. (1958[Wiley, R. H., Jarboe, C. H., Hayes, F. N., Hansbury, E., Nielsen, J. T., Callahan, P. X. & Sellars, M. (1958). J. Org. Chem. 23, 732-738.]); Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). For related structures, see: Butcher et al. (2007[Butcher, R. J., Jasinski, J. P., Prasad, D. J., Narayana, B. & Yathirajan, H. S. (2007). Acta Cryst. E63, o4005-o4006.]); Fun, Quah et al. (2009[Fun, H.-K., Quah, C. K., Sarveswari, S., Vijayakumar, V. & Prasath, R. (2009). Acta Cryst. E65, o2707-o2708.]); Fun, Yeap et al. (2009[Fun, H.-K., Yeap, C. S., Sarveswari, S., Vijayakumar, V. & Prasath, R. (2009). Acta Cryst. E65, o2665-o2666.]); Fun et al. (2010[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o582-o583.]); Guo et al. (2006[Guo, H.-M., Jian, F.-F., Zhou, L.-Y., Zhao, P.-S. & Zheng, J. (2006). Acta Cryst. E62, o4337-o4338.], 2007[Guo, H.-M., Jian, F.-F., Wang, L., Li, L.-M. & Wu, Q. (2007). Acta Cryst. E63, o1908-o1909.]); Li (2007a[Li, H. (2007a). Acta Cryst. E63, o3280.],b[Li, H. (2007b). Acta Cryst. E63, o3499.]); Loh et al. (2010[Loh, W.-S., Fun, H.-K., Sarveswari, S., Vijayakumar, V. & Reddy, B. P. (2010). Acta Cryst. E66, o304.]); Yathirajan et al. (2007a[Yathirajan, H. S., Bindya, S., Sarojini, B. K., Narayana, B. & Bolte, M. (2007a). Acta Cryst. E63, o2566.],b[Yathirajan, H. S., Bindya, S., Sarojini, B. K., Narayana, B. & Bolte, M. (2007b). Acta Cryst. E63, o2718.]).

[Scheme 1]

Experimental

Crystal data
  • C21H16F2N2

  • Mr = 334.36

  • Monoclinic, P 21 /c

  • a = 12.2880 (3) Å

  • b = 13.1678 (3) Å

  • c = 11.3245 (3) Å

  • β = 112.661 (3)°

  • V = 1690.91 (7) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.77 mm−1

  • T = 100 K

  • 0.28 × 0.24 × 0.23 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]) Tmin = 0.774, Tmax = 1.000

  • 7737 measured reflections

  • 3541 independent reflections

  • 2740 reflections with I > 2σ(I)

  • Rint = 0.016

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.116

  • S = 1.05

  • 3541 reflections

  • 226 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
YXCg π ring inter­actions (Å, °)

Cg4 is the centroid of ring C16–C21 and Cg2 is the centroid of the ring C1–C6.

XHCgX XCg H⋯Cg X⋯Perp
C9—H9⋯Cg4i 3.6677 (16) 2.82 2.76
C12—H12⋯Cg2ii 3.6061 (18) 2.88 −2.79
Symmetry codes: (i) 1 − x, 1 − y, 1 − z; (ii) −x, −[{1\over 2}] + y, [{1\over 2}] − z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); data reduction: CrysAlis RED; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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

Pyrazolines are well known as important nitrogen-containing five-membered heterocyclic compounds and various methods have been worked out for their synthesis (Fustero et al., 2009). The pyrazoline function is quite stable and has inspired chemists to utilize this stable fragment in bioactive moieties to synthesize new compounds possessing biological activities, and the presence of fluorine in the molecules at strategic positions alters their activity. Several pyrazoline derivatives have been found to possess considerable biological activities, which stimulated research activity in this field. In particular, they are used as antitumor, antibacterial, antifungal, antiviral, anti-parasitic, anti-tubercular and insecticidal agents (Hes et al., 1978; Amir et al., 2008). Some of these compounds have also anti-inflammatory, anti-diabetic, anaesthetic and analgesic properties (Sarojini et al., 2010; Regaila et al., 1979). Several 1,3,5-triaryl-2 -pyrazolines were also used as scintillation solutes (Wiley et al., 1958). In addition, pyrazolines have played a crucial part in the development of theory in heterocyclic chemistry and also used extensively in organic synthesis (Klimova et al., 1999; Bhaskarreddy et al., 1997).

The crystal structures of some substituted 4,5-dihydro N– phenyl pyrazoles viz., 6-chloro-3-[5-(4-fluorophenyl)-1-phenyl-4,5- dihydro-1H-pyrazol-3-yl]-2-methyl-4-phenyl quinoline (Loh et al., 2010), 6-chloro-3-[5-(3-methoxy-8-methyl-4- quinolyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-2-methyl-4-phenyl quinoline (Fun et al., 2009a), 6-chloro-2-methyl-4-phenyl- 3-[1-phenyl-5-(2-thienyl)-4,5-dihydro-1H-pyrazol-3-yl] quinoline (Fun et al., 2009b), 3-(4-fluorophenyl)-1,5-diphenyl-2-pyrazoline (Guo et al., 2006), 3-(4-bromophenyl)-5- (2-chlorophenyl)-1-phenyl-2-pyrazoline, (Guo et al., 2007), 5-(p-fluorophenyl)-1,3-diphenyl-2-pyrazoline, 3-(4-bromophenyl)-5 -(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole (Li, 2007a,b) have been reported. In continuation of our work on pyrazoline derivatives (Fun et al., 2010; Yathirajan et al., 2007a,b; Butcher et al., 2007) and in view of the importance of these derivatives, the title compound C21H15N2F2 (I) was synthesized and its crystal structure is reported here.

The title compound (I) contains two p-florophenyl groups and a benzene ring attached to an envelope configured pyrazole ring (Fig. 1). The dihedral angle between the two flourophenyl groups is 66.34 (8)° and the dihedral angle between the pyrazole and benzene rings is 11.50 (9) °. Also, the dihedral angles between the benzene ring and the two fluoro-substituted phenyl groups are 77.7 (6) and 16.7 (5) °, respectively. Two C–H···π interactions (Table 1) contribute to the stability of the crystal structure (Fig. 2).

Related literature top

For background to the chemistry and biological activity of pyrazolines, see: Amir et al. (2008); Bhaskarreddy et al. (1997); Fustero et al. (2009); Hes et al. (1978); Klimova et al. (1999); Regaila et al. (1979); Sarojini et al., (2010); Wiley et al. (1958); Spek (2009). For related structures, see: Butcher et al. (2007); Fun, Quah et al. (2009); Fun, Yeap et al. (2009); Fun et al. (2010); Guo et al. (2006, 2007); Li (2007a,b); Loh et al. (2010); Yathirajan et al. (2007a,b).

Experimental top

A mixture of (2E)-1,3-bis(4-fluorophenyl)prop-2-en-1-one (2.44 g, 0.01 mol) and phenyl hydrazine (1.08 g, 0.01 mol) in ethanol (20 ml) in the presence of glacial acetic acid (5 ml) was refluxed for 5 h. The reaction mixture was cooled and poured into ice-cold water (50 ml). The precipitate was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from toluene by the slow evaporation method. The yield of the compound was 84%; m.pt. 387 K. Analytical data: Found (Calculated): C %: 67.86 (67.99); H %: 4.62 (4.70); N %: 9.29 (9.33).

Refinement top

All of the H atoms were placed in their calculated positions and then refined using the riding model approximation with C—H = 0.93–0.98 Å, and with Uiso(H) = 1.19–1.30Ueq(C).

Structure description top

Pyrazolines are well known as important nitrogen-containing five-membered heterocyclic compounds and various methods have been worked out for their synthesis (Fustero et al., 2009). The pyrazoline function is quite stable and has inspired chemists to utilize this stable fragment in bioactive moieties to synthesize new compounds possessing biological activities, and the presence of fluorine in the molecules at strategic positions alters their activity. Several pyrazoline derivatives have been found to possess considerable biological activities, which stimulated research activity in this field. In particular, they are used as antitumor, antibacterial, antifungal, antiviral, anti-parasitic, anti-tubercular and insecticidal agents (Hes et al., 1978; Amir et al., 2008). Some of these compounds have also anti-inflammatory, anti-diabetic, anaesthetic and analgesic properties (Sarojini et al., 2010; Regaila et al., 1979). Several 1,3,5-triaryl-2 -pyrazolines were also used as scintillation solutes (Wiley et al., 1958). In addition, pyrazolines have played a crucial part in the development of theory in heterocyclic chemistry and also used extensively in organic synthesis (Klimova et al., 1999; Bhaskarreddy et al., 1997).

The crystal structures of some substituted 4,5-dihydro N– phenyl pyrazoles viz., 6-chloro-3-[5-(4-fluorophenyl)-1-phenyl-4,5- dihydro-1H-pyrazol-3-yl]-2-methyl-4-phenyl quinoline (Loh et al., 2010), 6-chloro-3-[5-(3-methoxy-8-methyl-4- quinolyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-2-methyl-4-phenyl quinoline (Fun et al., 2009a), 6-chloro-2-methyl-4-phenyl- 3-[1-phenyl-5-(2-thienyl)-4,5-dihydro-1H-pyrazol-3-yl] quinoline (Fun et al., 2009b), 3-(4-fluorophenyl)-1,5-diphenyl-2-pyrazoline (Guo et al., 2006), 3-(4-bromophenyl)-5- (2-chlorophenyl)-1-phenyl-2-pyrazoline, (Guo et al., 2007), 5-(p-fluorophenyl)-1,3-diphenyl-2-pyrazoline, 3-(4-bromophenyl)-5 -(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole (Li, 2007a,b) have been reported. In continuation of our work on pyrazoline derivatives (Fun et al., 2010; Yathirajan et al., 2007a,b; Butcher et al., 2007) and in view of the importance of these derivatives, the title compound C21H15N2F2 (I) was synthesized and its crystal structure is reported here.

The title compound (I) contains two p-florophenyl groups and a benzene ring attached to an envelope configured pyrazole ring (Fig. 1). The dihedral angle between the two flourophenyl groups is 66.34 (8)° and the dihedral angle between the pyrazole and benzene rings is 11.50 (9) °. Also, the dihedral angles between the benzene ring and the two fluoro-substituted phenyl groups are 77.7 (6) and 16.7 (5) °, respectively. Two C–H···π interactions (Table 1) contribute to the stability of the crystal structure (Fig. 2).

For background to the chemistry and biological activity of pyrazolines, see: Amir et al. (2008); Bhaskarreddy et al. (1997); Fustero et al. (2009); Hes et al. (1978); Klimova et al. (1999); Regaila et al. (1979); Sarojini et al., (2010); Wiley et al. (1958); Spek (2009). For related structures, see: Butcher et al. (2007); Fun, Quah et al. (2009); Fun, Yeap et al. (2009); Fun et al. (2010); Guo et al. (2006, 2007); Li (2007a,b); Loh et al. (2010); Yathirajan et al. (2007a,b).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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. Molecular structure of (I), with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram for (I), viewed down the c axis.
3,5-Bis(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole top
Crystal data top
C21H16F2N2F(000) = 696
Mr = 334.36Dx = 1.313 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 3839 reflections
a = 12.2880 (3) Åθ = 4.5–77.2°
b = 13.1678 (3) ŵ = 0.77 mm1
c = 11.3245 (3) ÅT = 100 K
β = 112.661 (3)°Block, colorless
V = 1690.91 (7) Å30.28 × 0.24 × 0.23 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Ruby (Gemini Cu) detector
3541 independent reflections
Radiation source: fine-focus sealed tube2740 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 10.5081 pixels mm-1θmax = 77.4°, θmin = 5.2°
ω scansh = 1115
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 1614
Tmin = 0.774, Tmax = 1.000l = 1314
7737 measured reflections
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.060P)2 + 0.1618P]
where P = (Fo2 + 2Fc2)/3
3541 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C21H16F2N2V = 1690.91 (7) Å3
Mr = 334.36Z = 4
Monoclinic, P21/cCu Kα radiation
a = 12.2880 (3) ŵ = 0.77 mm1
b = 13.1678 (3) ÅT = 100 K
c = 11.3245 (3) Å0.28 × 0.24 × 0.23 mm
β = 112.661 (3)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Ruby (Gemini Cu) detector
3541 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
2740 reflections with I > 2σ(I)
Tmin = 0.774, Tmax = 1.000Rint = 0.016
7737 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.05Δρmax = 0.15 e Å3
3541 reflectionsΔρmin = 0.16 e Å3
226 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
F10.14722 (10)0.03973 (7)0.26845 (11)0.0891 (3)
F20.03475 (11)0.92804 (9)0.61215 (12)0.0958 (4)
N10.27887 (10)0.60196 (9)0.37791 (11)0.0583 (3)
N20.31295 (11)0.50566 (9)0.35601 (11)0.0594 (3)
C10.11598 (14)0.67082 (12)0.57694 (14)0.0649 (4)
H10.10900.60620.60640.078*
C20.06799 (15)0.75266 (13)0.61618 (15)0.0710 (4)
H20.02880.74370.67120.085*
C30.07946 (15)0.84700 (12)0.57224 (15)0.0682 (4)
C40.13479 (15)0.86269 (12)0.48921 (17)0.0725 (4)
H40.13980.92760.45930.087*
C50.18302 (14)0.78039 (12)0.45068 (15)0.0643 (4)
H50.22150.79020.39510.077*
C60.17452 (12)0.68283 (10)0.49427 (12)0.0549 (3)
C70.22462 (12)0.59450 (11)0.45457 (12)0.0554 (3)
C80.21469 (15)0.48688 (11)0.49360 (15)0.0644 (4)
H8A0.13530.46080.45050.077*
H8B0.23740.48120.58540.077*
C90.30233 (13)0.43192 (10)0.44948 (13)0.0563 (3)
H90.37850.42650.52180.068*
C100.26207 (11)0.32735 (10)0.39674 (12)0.0515 (3)
C110.18963 (13)0.31090 (11)0.26960 (13)0.0603 (3)
H110.16650.36540.21320.072*
C120.15145 (14)0.21357 (13)0.22594 (14)0.0658 (4)
H120.10390.20200.14050.079*
C130.18527 (14)0.13539 (11)0.31124 (15)0.0632 (4)
C140.25607 (15)0.14782 (11)0.43752 (15)0.0662 (4)
H140.27750.09290.49340.079*
C150.29473 (14)0.24498 (11)0.47929 (14)0.0605 (3)
H150.34370.25530.56460.073*
C160.39681 (12)0.49799 (11)0.30110 (13)0.0567 (3)
C170.46147 (13)0.40957 (13)0.31169 (15)0.0660 (4)
H170.45260.35560.36020.079*
C180.53935 (14)0.40141 (15)0.25016 (18)0.0769 (5)
H180.58180.34170.25730.092*
C190.55439 (16)0.48058 (17)0.17879 (18)0.0853 (5)
H190.60600.47450.13690.102*
C200.49212 (17)0.56887 (17)0.17010 (18)0.0838 (5)
H200.50320.62310.12320.101*
C210.41337 (15)0.57872 (13)0.22966 (15)0.0679 (4)
H210.37160.63890.22220.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.1227 (8)0.0572 (5)0.1070 (7)0.0245 (5)0.0660 (7)0.0303 (5)
F20.1130 (8)0.0748 (7)0.1084 (8)0.0252 (6)0.0524 (7)0.0023 (6)
N10.0659 (6)0.0496 (6)0.0595 (6)0.0020 (5)0.0243 (5)0.0031 (5)
N20.0710 (7)0.0487 (6)0.0649 (6)0.0046 (5)0.0332 (6)0.0029 (5)
C10.0796 (9)0.0579 (8)0.0594 (8)0.0042 (7)0.0292 (7)0.0100 (6)
C20.0806 (10)0.0748 (11)0.0610 (8)0.0123 (8)0.0309 (7)0.0080 (7)
C30.0734 (9)0.0615 (9)0.0660 (8)0.0099 (7)0.0226 (7)0.0019 (7)
C40.0819 (10)0.0501 (8)0.0846 (10)0.0001 (7)0.0310 (8)0.0051 (7)
C50.0739 (9)0.0559 (8)0.0653 (8)0.0043 (7)0.0294 (7)0.0037 (6)
C60.0608 (7)0.0511 (7)0.0482 (6)0.0024 (6)0.0160 (5)0.0006 (5)
C70.0637 (7)0.0505 (7)0.0492 (6)0.0054 (6)0.0186 (6)0.0013 (5)
C80.0879 (10)0.0489 (7)0.0653 (8)0.0086 (7)0.0392 (8)0.0038 (6)
C90.0655 (7)0.0490 (7)0.0521 (7)0.0080 (6)0.0199 (6)0.0009 (5)
C100.0568 (7)0.0468 (6)0.0521 (6)0.0041 (5)0.0224 (5)0.0005 (5)
C110.0666 (8)0.0574 (8)0.0536 (7)0.0053 (6)0.0193 (6)0.0030 (6)
C120.0689 (8)0.0707 (9)0.0574 (8)0.0129 (7)0.0238 (7)0.0140 (7)
C130.0790 (9)0.0481 (7)0.0783 (9)0.0110 (7)0.0479 (8)0.0148 (7)
C140.0893 (10)0.0472 (7)0.0713 (9)0.0007 (7)0.0409 (8)0.0036 (6)
C150.0748 (8)0.0518 (7)0.0532 (7)0.0019 (6)0.0229 (6)0.0018 (6)
C160.0554 (7)0.0578 (8)0.0543 (7)0.0101 (6)0.0183 (6)0.0038 (6)
C170.0608 (7)0.0643 (9)0.0730 (9)0.0073 (7)0.0260 (7)0.0002 (7)
C180.0634 (8)0.0789 (11)0.0888 (11)0.0029 (8)0.0296 (8)0.0106 (9)
C190.0762 (10)0.1065 (15)0.0854 (11)0.0113 (10)0.0445 (9)0.0060 (11)
C200.0886 (11)0.0945 (13)0.0772 (11)0.0122 (10)0.0420 (9)0.0117 (9)
C210.0735 (9)0.0678 (9)0.0649 (8)0.0065 (7)0.0295 (7)0.0055 (7)
Geometric parameters (Å, º) top
F1—C131.3658 (16)C9—H90.9800
F2—C31.3551 (19)C10—C151.3865 (19)
N1—C71.2859 (19)C10—C111.3873 (19)
N1—N21.3875 (17)C11—C121.389 (2)
N2—C161.3973 (19)C11—H110.9300
N2—C91.4787 (17)C12—C131.363 (2)
C1—C21.382 (2)C12—H120.9300
C1—C61.392 (2)C13—C141.367 (2)
C1—H10.9300C14—C151.383 (2)
C2—C31.366 (2)C14—H140.9300
C2—H20.9300C15—H150.9300
C3—C41.372 (3)C16—C171.388 (2)
C4—C51.384 (2)C16—C211.398 (2)
C4—H40.9300C17—C181.388 (2)
C5—C61.395 (2)C17—H170.9300
C5—H50.9300C18—C191.374 (3)
C6—C71.465 (2)C18—H180.9300
C7—C81.503 (2)C19—C201.374 (3)
C8—C91.532 (2)C19—H190.9300
C8—H8A0.9700C20—C211.382 (3)
C8—H8B0.9700C20—H200.9300
C9—C101.5066 (18)C21—H210.9300
C7—N1—N2108.75 (11)C15—C10—C11118.74 (13)
N1—N2—C16118.08 (11)C15—C10—C9118.83 (12)
N1—N2—C9110.87 (11)C11—C10—C9122.38 (12)
C16—N2—C9123.69 (12)C10—C11—C12120.48 (13)
C2—C1—C6121.53 (15)C10—C11—H11119.8
C2—C1—H1119.2C12—C11—H11119.8
C6—C1—H1119.2C13—C12—C11118.43 (13)
C3—C2—C1118.40 (16)C13—C12—H12120.8
C3—C2—H2120.8C11—C12—H12120.8
C1—C2—H2120.8C12—C13—F1118.43 (14)
F2—C3—C2118.86 (16)C12—C13—C14123.25 (13)
F2—C3—C4118.80 (15)F1—C13—C14118.31 (14)
C2—C3—C4122.34 (15)C13—C14—C15117.69 (14)
C3—C4—C5118.93 (15)C13—C14—H14121.2
C3—C4—H4120.5C15—C14—H14121.2
C5—C4—H4120.5C14—C15—C10121.40 (13)
C4—C5—C6120.67 (15)C14—C15—H15119.3
C4—C5—H5119.7C10—C15—H15119.3
C6—C5—H5119.7C17—C16—N2121.18 (13)
C1—C6—C5118.12 (14)C17—C16—C21118.80 (14)
C1—C6—C7120.21 (13)N2—C16—C21119.97 (14)
C5—C6—C7121.67 (13)C18—C17—C16120.26 (16)
N1—C7—C6122.33 (13)C18—C17—H17119.9
N1—C7—C8113.11 (13)C16—C17—H17119.9
C6—C7—C8124.52 (13)C19—C18—C17120.75 (18)
C7—C8—C9101.68 (12)C19—C18—H18119.6
C7—C8—H8A111.4C17—C18—H18119.6
C9—C8—H8A111.4C20—C19—C18119.11 (17)
C7—C8—H8B111.4C20—C19—H19120.4
C9—C8—H8B111.4C18—C19—H19120.4
H8A—C8—H8B109.3C19—C20—C21121.30 (17)
N2—C9—C10114.99 (11)C19—C20—H20119.4
N2—C9—C8100.96 (11)C21—C20—H20119.4
C10—C9—C8113.34 (11)C20—C21—C16119.77 (17)
N2—C9—H9109.1C20—C21—H21120.1
C10—C9—H9109.1C16—C21—H21120.1
C8—C9—H9109.1
C7—N1—N2—C16164.89 (12)N2—C9—C10—C15153.43 (13)
C7—N1—N2—C913.70 (16)C8—C9—C10—C1591.13 (16)
C6—C1—C2—C30.2 (2)N2—C9—C10—C1129.19 (19)
C1—C2—C3—F2178.70 (14)C8—C9—C10—C1186.26 (17)
C1—C2—C3—C41.2 (3)C15—C10—C11—C120.5 (2)
F2—C3—C4—C5178.47 (14)C9—C10—C11—C12177.88 (13)
C2—C3—C4—C51.4 (3)C10—C11—C12—C131.0 (2)
C3—C4—C5—C60.7 (2)C11—C12—C13—F1179.67 (13)
C2—C1—C6—C50.5 (2)C11—C12—C13—C140.8 (2)
C2—C1—C6—C7179.91 (14)C12—C13—C14—C150.1 (2)
C4—C5—C6—C10.2 (2)F1—C13—C14—C15179.47 (14)
C4—C5—C6—C7179.85 (14)C13—C14—C15—C100.7 (2)
N2—N1—C7—C6178.39 (12)C11—C10—C15—C140.4 (2)
N2—N1—C7—C80.60 (16)C9—C10—C15—C14177.09 (14)
C1—C6—C7—N1179.65 (13)N1—N2—C16—C17160.01 (13)
C5—C6—C7—N10.0 (2)C9—N2—C16—C1712.8 (2)
C1—C6—C7—C82.1 (2)N1—N2—C16—C2122.60 (19)
C5—C6—C7—C8177.51 (14)C9—N2—C16—C21169.85 (13)
N1—C7—C8—C913.51 (16)N2—C16—C17—C18176.23 (14)
C6—C7—C8—C9168.75 (12)C21—C16—C17—C181.2 (2)
N1—N2—C9—C10143.41 (12)C16—C17—C18—C190.5 (2)
C16—N2—C9—C1067.31 (17)C17—C18—C19—C200.7 (3)
N1—N2—C9—C821.03 (14)C18—C19—C20—C211.2 (3)
C16—N2—C9—C8170.31 (12)C19—C20—C21—C160.5 (3)
C7—C8—C9—N219.28 (13)C17—C16—C21—C200.7 (2)
C7—C8—C9—C10142.80 (12)N2—C16—C21—C20176.72 (15)

Experimental details

Crystal data
Chemical formulaC21H16F2N2
Mr334.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)12.2880 (3), 13.1678 (3), 11.3245 (3)
β (°) 112.661 (3)
V3)1690.91 (7)
Z4
Radiation typeCu Kα
µ (mm1)0.77
Crystal size (mm)0.28 × 0.24 × 0.23
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Ruby (Gemini Cu) detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.774, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
7737, 3541, 2740
Rint0.016
(sin θ/λ)max1)0.633
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.116, 1.05
No. of reflections3541
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.16

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Y-X···Cg π ring interactions, Cg4 is the centroid of ring C16-C21, and Cg2 is the centroid of the ring C1-C6. [Symmetry codes: (i) 1-x,1-y,1-z ; (ii) -x,-1/2+y,1/2-z] top
XH···CgX (Å)X···Cg, (Å)H···CgX···Perp (Å)
C9–H9···Cg4i3.6677 (16)2.822.76
C12–H12···Cg223.6061 (18)2.88-2.79
 

Acknowledgements

SS thanks Mangalore University for research facilities and HSY thanks the University of Mysore for sabbatical leave. JPJ thanks Dr Ray Butcher and Howard University for assistance with the data collection.

References

First citationAmir, M., Kumar, H. & Khan, S. A. (2008). Bioorg. Med. Chem. Lett. 18, 918–922.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBhaskarreddy, D., Chandrasekhar, B. N., Padmavathi, V. & Sumathi, R. P. (1997). Synthesis, 3, 491–494.  Google Scholar
First citationButcher, R. J., Jasinski, J. P., Prasad, D. J., Narayana, B. & Yathirajan, H. S. (2007). Acta Cryst. E63, o4005–o4006.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o582–o583.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationFun, H.-K., Quah, C. K., Sarveswari, S., Vijayakumar, V. & Prasath, R. (2009). Acta Cryst. E65, o2707–o2708.  Web of Science CrossRef IUCr Journals Google Scholar
First citationFun, H.-K., Yeap, C. S., Sarveswari, S., Vijayakumar, V. & Prasath, R. (2009). Acta Cryst. E65, o2665–o2666.  Web of Science CrossRef IUCr Journals Google Scholar
First citationFustero, S., Fuentes, A. S. & Sanz-Cervera, J. F. (2009). Org. Prep. Proc. Int. 41, 253–290.  Web of Science CrossRef CAS Google Scholar
First citationGuo, H.-M., Jian, F.-F., Wang, L., Li, L.-M. & Wu, Q. (2007). Acta Cryst. E63, o1908–o1909.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGuo, H.-M., Jian, F.-F., Zhou, L.-Y., Zhao, P.-S. & Zheng, J. (2006). Acta Cryst. E62, o4337–o4338.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHes, R. V., Wellinga, K. & Grosscurt, A. C. (1978). J. Agric. Food Chem. 26, 915–918.  Google Scholar
First citationKlimova, E. I., Marcos, M., Klimova, T. B., Cecilio, A. T., Ruben, A. T. & Lena, R. R. (1999). J. Organomet. Chem. 585, 106–111.  Web of Science CSD CrossRef CAS Google Scholar
First citationLi, H. (2007a). Acta Cryst. E63, o3280.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLi, H. (2007b). Acta Cryst. E63, o3499.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLoh, W.-S., Fun, H.-K., Sarveswari, S., Vijayakumar, V. & Reddy, B. P. (2010). Acta Cryst. E66, o304.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationOxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.  Google Scholar
First citationRegaila, H. A., El-Bayonk, A. K. & Hammad, M. (1979). Egypt. J. Chem. 20, 197–202.  Google Scholar
First citationSarojini, B. K., Vidyagayatri, M., Darshanraj, C. G., Bharath, B. R. & Manjunatha, H. (2010). Lett. Drug Des. Discovery, 7, 214–224.  CrossRef 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
First citationWiley, R. H., Jarboe, C. H., Hayes, F. N., Hansbury, E., Nielsen, J. T., Callahan, P. X. & Sellars, M. (1958). J. Org. Chem. 23, 732–738.  CrossRef CAS Web of Science Google Scholar
First citationYathirajan, H. S., Bindya, S., Sarojini, B. K., Narayana, B. & Bolte, M. (2007a). Acta Cryst. E63, o2566.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYathirajan, H. S., Bindya, S., Sarojini, B. K., Narayana, B. & Bolte, M. (2007b). Acta Cryst. E63, o2718.  Web of Science CSD CrossRef 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