4,6-Bis(4-fluoro­phen­yl)-2-phenyl-1H-indazol-3(2H)-one

Butcher, R.J.; Akkurt, M.; Samshuddin, S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536811016369

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1346-o1347

doi:10.1107/S1600536811016369

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4,6-Bis(4-fluorophenyl)-2-phenyl-1H-indazol-3(2H)-one

R. J. Butcher,^a M. Akkurt,^b ^* S. Samshuddin,^c B. Narayana ^c and H. S. Yathirajan ^d

^aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 26 March 2011; accepted 29 April 2011; online 7 May 2011)

In the title compound, C₂₅H₁₆F₂N₂O, the pyrazole ring is almost planar (r.m.s. deviation = 0.028 Å) and makes a dihedral angle of 5.86 (11)° with the indazole benzene ring. The dihedral angle between the pyrazole ring and the unsubstituted phenyl ring is 28.19 (11)°. The dihedral angles between the unsubstituted phenyl and the two fluorophenyl groups are 57.69 (10) and 18.01 (10)°. In the crystal, molecules are linked by intermolecular N—H⋯O and C—H⋯F interactions, forming infinite chains along the b axis with graph-set motif R₃²(19). The crystal structure is further consolidated by π–π stacking [centroid–centroid distances = 3.5916 (13) and 3.6890 (13) Å] and C—H⋯π interactions.

Related literature

For the pharmacological activity of indazole derivatives, see: Beylin et al. (1991 ); George et al. (1998 ); Jain et al. (1987 ); Palazzo et al. (1966 ); Popat et al. (2003 ); Roman (1990 ). For related structures, see: van der Helm et al. (1979 ); Fun et al. (2010 ). For hybridization and electron delocalization around N atoms, see: Susindran et al. (2010 ); Jin et al. (2004 ). For graph-set analysis, see: Etter (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₅H₁₆F₂N₂O
M_r = 398.40
Orthorhombic, P b c n
a = 15.2947 (4) Å
b = 11.6259 (2) Å
c = 20.9388 (5) Å
V = 3723.23 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 123 K
0.49 × 0.38 × 0.23 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.895, T_max = 0.977
19870 measured reflections
3827 independent reflections
3416 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.135
S = 1.09
3827 reflections
275 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg5 is the centroid of the C20–C25 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—HN2⋯O1ⁱ	0.86 (2)	2.00 (2)	2.830 (2)	162 (2)
C6—H6⋯F1ⁱⁱ	0.93	2.49	3.362 (2)	156
C15—H15⋯Cg5ⁱⁱⁱ	0.93	2.85	3.656 (2)	145
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) x, y+1, z; (iii) $[x, -y, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016369/qk2004sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016369/qk2004Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016369/qk2004Isup3.cml

checkCIF report

Comment top

In last few decades, much attention has been paid to the synthesis of heterocycles containing 1,2-diazole systems like indazole mainly due to their broad spectrum of pharmacological properties. Indazole derivatives possess variety of pharmacological activities such as analgesic, anti inflammatory, antidepressant, antihypertensive, antiviral and anticancer activities (Jain et al., 1987; Palazzo et al., 1966; Popat et al., 2003; Beylin et al., 1991; George et al., 1998; Roman, 1990).

The crystal structure of indazole derivative, viz., 1,2,4,5-tetrahydro-7-methoxy-3H-benz[g]indazol-3-one monohydrate (van der Helm et al., 1979) has been reported. Also the crystal structure of methyl 4,6-bis(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate, the precursor of the title compound, has been reported (Fun et al., 2010). In view of the importance of indazole derivatives, the title compound (I) is synthesized and its crystal structure is reported here.

The pyrazole ring (N1/N2/C1/C2/C7) in (I), (Fig. 1), is almost planar with the largest deviations from the mean plane being 0.039 (2) Å for C7 and -0.035 (2) Å for N2. The sum of the surrounding angles around N1 in the pyrazole ring is 358.15 (15)°, in accordance with the sp² hybridization of the N1 atom (Susindran et al., 2010). The C1—N1 and C7—N2 bond lengths in the pyrazole ring are 1.390 (2) and 1.367 (3) Å, respectively. The values of these distances are shorter than the pertinent single bond length of 1.443 Å and are longer than the double bond length of 1.269 Å (Jin et al., 2004). This case indicates electron delocalization.

The dihedral angle between the pyrazole ring and the indazole benzene ring in (I), (Fig. 1), is 5.86 (11)°. The dihedral angle between the two fluorophenyl groups is 42.56 (11)°, and the dihedral angle between the five-membered pyrazole ring and the unsubstituted phenyl ring is 28.19 (11)°. The unsubstituted phenyl ring and the two fluorophenyl groups make dihedral angles of 57.69 (10) and 18.01 (10)°, respectively, with each other.

In the crystal structure, molecules are linked by intermolecular N—H···O and C—H···F interactions, forming R²₃(19) graph-set motifs (Etter, 1990; Bernstein et al., 1995) along the b axis of the unit cell (Table 1, Fig. 2). In addition, the crystal structure is consolidated by C—H···π and π-π stacking [Cg1···Cg3(3/2 - x, 1/2 + y, z) = 3.5916 (13) Å and Cg3···Cg3(1 - x, y, 1/2 - z) = 3.6890 (13) Å; Cg1 and Cg3 are the centroids of the N1/N2/C1/C2/C7 pyrazole ring and C8—C13 benzene ring, respectively] interactions.

Related literature top

For the pharmacological activity of indazole derivatives, see: Beylin et al. (1991); George et al. (1998); Jain et al. (1987); Palazzo et al. (1966); Popat et al. (2003); Roman (1990). For related structures, see: van der Helm et al. (1979); Fun et al. (2010). For hybridization and electron delocalization around N atoms, see: Susindran et al. (2010); Jin et al. (2004). For graph-set analysis, see: Etter (1990); Bernstein et al. (1995).

Experimental top

A mixture of methyl 4,6-bis(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate (3.42 g, 0.01 mol) and phenyl hydrazine (1.08 g, 0.01 mol) in 50 ml e thanol containing 1 ml glacial acetic acid was refluxed for 10 h. The reaction mixture was cooled and poured into 50 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. Yellow prisms of (I) were grown from DMF by slow evaporation (m.p.: > 523 K, yield: 58%).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of the title structure viewed down the c axis. N—H···O and C—H···F hydrogen bondings (dashed lines) link the molecules, forming R²₃(19) graph-set motifs along the b axis of the unit cell. H atoms not involved in hydrogen bonds have been omitted for clarity.

4,6-Bis(4-fluorophenyl)-2-phenyl-1H-indazol-3(2H)-one top

Crystal data top

C₂₅H₁₆F₂N₂O	F(000) = 1648
M_r = 398.40	D_x = 1.421 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 11209 reflections
a = 15.2947 (4) Å	θ = 5.2–37.5°
b = 11.6259 (2) Å	µ = 0.10 mm⁻¹
c = 20.9388 (5) Å	T = 123 K
V = 3723.23 (15) Å³	Prism, colourless
Z = 8	0.49 × 0.38 × 0.23 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3827 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3416 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10.5081 pixels mm^-1	θ_max = 26.5°, θ_min = 5.2°
ω scans	h = −19→19
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −14→14
T_min = 0.895, T_max = 0.977	l = −26→26
19870 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0462P)² + 4.0317P] where P = (F_o² + 2F_c²)/3
3827 reflections	(Δ/σ)_max < 0.001
275 parameters	Δρ_max = 0.65 e Å⁻³
1 restraint	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₅H₁₆F₂N₂O	V = 3723.23 (15) Å³
M_r = 398.40	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 15.2947 (4) Å	µ = 0.10 mm⁻¹
b = 11.6259 (2) Å	T = 123 K
c = 20.9388 (5) Å	0.49 × 0.38 × 0.23 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3827 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	3416 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.977	R_int = 0.029
19870 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	1 restraint
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.65 e Å⁻³
3827 reflections	Δρ_min = −0.35 e Å⁻³
275 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.60370 (13)	−0.57691 (11)	0.22016 (9)	0.0656 (6)
F2	0.48986 (10)	0.29173 (14)	0.53611 (7)	0.0525 (5)
O1	0.73203 (11)	−0.14990 (12)	0.11749 (7)	0.0351 (5)
N1	0.72290 (11)	0.04878 (13)	0.11220 (7)	0.0239 (5)
N2	0.68782 (11)	0.13815 (13)	0.14893 (8)	0.0241 (5)
C1	0.70924 (15)	−0.05733 (16)	0.14107 (9)	0.0269 (6)
C2	0.66455 (14)	−0.03003 (16)	0.20027 (9)	0.0272 (6)
C3	0.63295 (16)	−0.10034 (17)	0.25063 (10)	0.0323 (6)
C4	0.60213 (13)	−0.04532 (16)	0.30476 (9)	0.0246 (5)
C5	0.60116 (12)	0.07752 (16)	0.31012 (9)	0.0230 (5)
C6	0.62766 (13)	0.14448 (16)	0.25935 (9)	0.0248 (6)
C7	0.65858 (13)	0.08914 (16)	0.20431 (9)	0.0241 (5)
C8	0.62753 (14)	−0.22733 (16)	0.24316 (9)	0.0257 (6)
C9	0.58886 (14)	−0.27250 (18)	0.18834 (10)	0.0291 (6)
C10	0.57996 (15)	−0.3901 (2)	0.18045 (11)	0.0355 (7)
C11	0.61074 (16)	−0.46066 (17)	0.22766 (12)	0.0382 (7)
C12	0.64919 (16)	−0.42035 (19)	0.28203 (12)	0.0391 (7)
C13	0.65705 (15)	−0.30264 (18)	0.28970 (10)	0.0315 (6)
C14	0.57027 (12)	0.13239 (17)	0.37010 (9)	0.0246 (6)
C15	0.58997 (14)	0.08541 (18)	0.42973 (10)	0.0302 (6)
C16	0.56348 (15)	0.1384 (2)	0.48586 (10)	0.0365 (7)
C17	0.51680 (14)	0.2389 (2)	0.48129 (10)	0.0355 (7)
C18	0.49559 (14)	0.28874 (19)	0.42389 (11)	0.0338 (6)
C19	0.52226 (13)	0.23481 (18)	0.36821 (10)	0.0280 (6)
C20	0.74707 (13)	0.07083 (15)	0.04813 (9)	0.0216 (5)
C21	0.71378 (14)	0.16740 (16)	0.01763 (9)	0.0257 (6)
C22	0.73814 (15)	0.19020 (17)	−0.04494 (9)	0.0303 (6)
C23	0.79396 (15)	0.11777 (17)	−0.07719 (10)	0.0303 (6)
C24	0.82668 (15)	0.02163 (18)	−0.04644 (10)	0.0320 (6)
C25	0.80400 (13)	−0.00225 (17)	0.01629 (10)	0.0279 (6)
HN2	0.7174 (14)	0.2009 (14)	0.1477 (12)	0.038 (7)*
H4	0.58140	−0.08940	0.33860	0.0300*
H6	0.62510	0.22430	0.26150	0.0300*
H9	0.56880	−0.22300	0.15670	0.0350*
H10	0.55380	−0.42030	0.14400	0.0430*
H12	0.66960	−0.47070	0.31310	0.0470*
H13	0.68250	−0.27360	0.32670	0.0380*
H15	0.62150	0.01710	0.43190	0.0360*
H16	0.57700	0.10670	0.52540	0.0440*
H18	0.46410	0.35710	0.42240	0.0400*
H19	0.50800	0.26720	0.32890	0.0340*
H21	0.67550	0.21630	0.03890	0.0310*
H22	0.71650	0.25530	−0.06540	0.0360*
H23	0.80960	0.13330	−0.11920	0.0360*
H24	0.86430	−0.02760	−0.06810	0.0380*
H25	0.82670	−0.06660	0.03680	0.0330*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0954 (13)	0.0186 (7)	0.0829 (12)	−0.0145 (7)	0.0149 (10)	−0.0064 (7)
F2	0.0579 (9)	0.0652 (10)	0.0345 (7)	0.0125 (8)	0.0096 (7)	−0.0210 (7)
O1	0.0646 (11)	0.0155 (7)	0.0251 (7)	0.0055 (7)	0.0088 (7)	0.0007 (6)
N1	0.0364 (9)	0.0141 (7)	0.0213 (8)	0.0030 (7)	0.0009 (7)	−0.0001 (6)
N2	0.0366 (9)	0.0142 (7)	0.0216 (8)	0.0004 (7)	0.0023 (7)	−0.0007 (6)
C1	0.0440 (12)	0.0172 (9)	0.0195 (9)	0.0009 (8)	0.0002 (8)	0.0024 (7)
C2	0.0421 (11)	0.0179 (9)	0.0216 (9)	0.0008 (8)	0.0008 (8)	−0.0011 (7)
C3	0.0489 (13)	0.0216 (10)	0.0265 (10)	−0.0039 (9)	0.0052 (9)	0.0002 (8)
C4	0.0311 (10)	0.0216 (9)	0.0210 (9)	−0.0026 (8)	0.0005 (8)	0.0014 (7)
C5	0.0253 (9)	0.0225 (9)	0.0213 (9)	0.0023 (7)	−0.0030 (8)	−0.0027 (7)
C6	0.0344 (11)	0.0149 (8)	0.0250 (10)	0.0026 (7)	−0.0019 (8)	−0.0011 (7)
C7	0.0326 (10)	0.0177 (9)	0.0220 (9)	−0.0008 (8)	−0.0024 (8)	0.0011 (7)
C8	0.0365 (11)	0.0184 (9)	0.0222 (9)	−0.0025 (8)	0.0058 (8)	−0.0002 (7)
C9	0.0345 (11)	0.0292 (10)	0.0237 (10)	0.0015 (9)	0.0011 (9)	0.0034 (8)
C10	0.0384 (12)	0.0360 (12)	0.0321 (11)	−0.0130 (10)	0.0035 (9)	−0.0104 (9)
C11	0.0496 (14)	0.0153 (9)	0.0496 (14)	−0.0070 (9)	0.0130 (11)	−0.0019 (9)
C12	0.0503 (14)	0.0262 (11)	0.0407 (13)	0.0018 (10)	0.0019 (11)	0.0134 (10)
C13	0.0417 (12)	0.0291 (11)	0.0238 (10)	−0.0061 (9)	−0.0023 (9)	0.0046 (8)
C14	0.0247 (9)	0.0246 (10)	0.0244 (10)	−0.0009 (7)	−0.0005 (8)	−0.0038 (8)
C15	0.0351 (11)	0.0303 (10)	0.0253 (10)	0.0051 (9)	0.0007 (9)	−0.0019 (8)
C16	0.0419 (13)	0.0449 (13)	0.0228 (10)	0.0039 (10)	0.0002 (9)	−0.0021 (9)
C17	0.0329 (11)	0.0451 (13)	0.0284 (11)	0.0006 (10)	0.0059 (9)	−0.0150 (10)
C18	0.0283 (10)	0.0330 (11)	0.0400 (12)	0.0068 (9)	0.0025 (9)	−0.0083 (10)
C19	0.0261 (10)	0.0292 (10)	0.0287 (10)	0.0027 (8)	−0.0029 (8)	−0.0039 (8)
C20	0.0276 (9)	0.0180 (9)	0.0191 (9)	−0.0041 (7)	−0.0018 (7)	0.0010 (7)
C21	0.0368 (11)	0.0191 (9)	0.0213 (9)	0.0043 (8)	−0.0013 (8)	−0.0022 (7)
C22	0.0479 (13)	0.0206 (9)	0.0223 (10)	0.0003 (9)	−0.0040 (9)	0.0026 (8)
C23	0.0452 (12)	0.0243 (10)	0.0215 (9)	−0.0072 (9)	0.0054 (9)	0.0021 (8)
C24	0.0370 (11)	0.0273 (11)	0.0318 (11)	0.0024 (9)	0.0095 (9)	−0.0007 (9)
C25	0.0317 (10)	0.0221 (9)	0.0298 (10)	0.0028 (8)	0.0011 (8)	0.0037 (8)

Geometric parameters (Å, º) top

F1—C11	1.365 (2)	C15—C16	1.387 (3)
F2—C17	1.366 (3)	C16—C17	1.373 (3)
O1—C1	1.234 (2)	C17—C18	1.373 (3)
N1—N2	1.400 (2)	C18—C19	1.385 (3)
N1—C1	1.390 (2)	C20—C25	1.387 (3)
N1—C20	1.415 (2)	C20—C21	1.388 (3)
N2—C7	1.367 (3)	C21—C22	1.388 (3)
N2—HN2	0.859 (18)	C22—C23	1.376 (3)
C1—C2	1.451 (3)	C23—C24	1.384 (3)
C2—C3	1.419 (3)	C24—C25	1.387 (3)
C2—C7	1.391 (3)	C4—H4	0.9300
C3—C4	1.384 (3)	C6—H6	0.9300
C3—C8	1.487 (3)	C9—H9	0.9300
C4—C5	1.433 (3)	C10—H10	0.9300
C5—C14	1.486 (3)	C12—H12	0.9300
C5—C6	1.379 (3)	C13—H13	0.9300
C6—C7	1.402 (3)	C15—H15	0.9300
C8—C13	1.386 (3)	C16—H16	0.9300
C8—C9	1.394 (3)	C18—H18	0.9300
C9—C10	1.384 (3)	C19—H19	0.9300
C10—C11	1.368 (3)	C21—H21	0.9300
C11—C12	1.364 (3)	C22—H22	0.9300
C12—C13	1.383 (3)	C23—H23	0.9300
C14—C15	1.396 (3)	C24—H24	0.9300
C14—C19	1.400 (3)	C25—H25	0.9300

N2—N1—C1	111.25 (15)	C17—C18—C19	118.4 (2)
N2—N1—C20	119.12 (14)	C14—C19—C18	121.05 (19)
C1—N1—C20	127.78 (15)	N1—C20—C21	119.13 (17)
N1—N2—C7	106.38 (14)	C21—C20—C25	120.29 (18)
C7—N2—HN2	123.5 (17)	N1—C20—C25	120.58 (17)
N1—N2—HN2	114.3 (15)	C20—C21—C22	119.36 (18)
N1—C1—C2	104.38 (15)	C21—C22—C23	120.86 (19)
O1—C1—C2	131.73 (18)	C22—C23—C24	119.36 (19)
O1—C1—N1	123.89 (18)	C23—C24—C25	120.8 (2)
C1—C2—C3	132.02 (18)	C20—C25—C24	119.32 (18)
C1—C2—C7	107.51 (16)	C3—C4—H4	119.00
C3—C2—C7	120.41 (18)	C5—C4—H4	119.00
C2—C3—C4	117.28 (18)	C5—C6—H6	121.00
C4—C3—C8	121.73 (18)	C7—C6—H6	121.00
C2—C3—C8	120.85 (18)	C8—C9—H9	120.00
C3—C4—C5	121.89 (18)	C10—C9—H9	120.00
C4—C5—C6	119.97 (17)	C9—C10—H10	121.00
C4—C5—C14	119.84 (17)	C11—C10—H10	121.00
C6—C5—C14	120.19 (17)	C11—C12—H12	121.00
C5—C6—C7	118.29 (17)	C13—C12—H12	121.00
C2—C7—C6	121.95 (17)	C8—C13—H13	120.00
N2—C7—C6	128.04 (17)	C12—C13—H13	119.00
N2—C7—C2	110.00 (16)	C14—C15—H15	119.00
C3—C8—C13	122.36 (18)	C16—C15—H15	119.00
C9—C8—C13	118.64 (18)	C15—C16—H16	121.00
C3—C8—C9	118.97 (18)	C17—C16—H16	121.00
C8—C9—C10	120.81 (19)	C17—C18—H18	121.00
C9—C10—C11	118.2 (2)	C19—C18—H18	121.00
F1—C11—C10	118.9 (2)	C14—C19—H19	119.00
C10—C11—C12	123.0 (2)	C18—C19—H19	119.00
F1—C11—C12	118.0 (2)	C20—C21—H21	120.00
C11—C12—C13	118.3 (2)	C22—C21—H21	120.00
C8—C13—C12	121.0 (2)	C21—C22—H22	120.00
C15—C14—C19	118.13 (18)	C23—C22—H22	119.00
C5—C14—C15	121.30 (18)	C22—C23—H23	120.00
C5—C14—C19	120.55 (17)	C24—C23—H23	120.00
C14—C15—C16	121.40 (19)	C23—C24—H24	120.00
C15—C16—C17	118.1 (2)	C25—C24—H24	120.00
F2—C17—C18	118.3 (2)	C20—C25—H25	120.00
C16—C17—C18	122.9 (2)	C24—C25—H25	120.00
F2—C17—C16	118.77 (19)

C1—N1—N2—C7	5.3 (2)	C6—C5—C14—C19	35.8 (3)
C20—N1—N2—C7	171.01 (17)	C4—C5—C14—C19	−143.24 (19)
N2—N1—C1—O1	178.1 (2)	C4—C5—C6—C7	−2.7 (3)
C20—N1—C1—O1	14.0 (3)	C4—C5—C14—C15	38.4 (3)
N2—N1—C1—C2	−1.4 (2)	C5—C6—C7—N2	179.9 (2)
C20—N1—C1—C2	−165.57 (19)	C5—C6—C7—C2	−1.2 (3)
C1—N1—C20—C25	−35.8 (3)	C3—C8—C9—C10	−177.9 (2)
N2—N1—C20—C21	−18.2 (3)	C3—C8—C13—C12	178.4 (2)
C1—N1—C20—C21	144.9 (2)	C9—C8—C13—C12	0.5 (3)
N2—N1—C20—C25	161.15 (18)	C13—C8—C9—C10	0.1 (3)
N1—N2—C7—C6	171.78 (19)	C8—C9—C10—C11	−0.5 (3)
N1—N2—C7—C2	−7.2 (2)	C9—C10—C11—F1	−179.0 (2)
N1—C1—C2—C3	−180.0 (2)	C9—C10—C11—C12	0.4 (4)
N1—C1—C2—C7	−3.0 (2)	C10—C11—C12—C13	0.2 (4)
O1—C1—C2—C3	0.5 (4)	F1—C11—C12—C13	179.6 (2)
O1—C1—C2—C7	177.5 (2)	C11—C12—C13—C8	−0.7 (4)
C1—C2—C7—C6	−172.62 (19)	C19—C14—C15—C16	−0.4 (3)
C1—C2—C7—N2	6.4 (2)	C5—C14—C19—C18	−177.86 (19)
C1—C2—C3—C4	172.4 (2)	C5—C14—C15—C16	178.00 (19)
C3—C2—C7—N2	−176.14 (19)	C15—C14—C19—C18	0.5 (3)
C3—C2—C7—C6	4.8 (3)	C14—C15—C16—C17	0.2 (3)
C7—C2—C3—C8	171.4 (2)	C15—C16—C17—F2	179.7 (2)
C1—C2—C3—C8	−11.9 (4)	C15—C16—C17—C18	−0.1 (3)
C7—C2—C3—C4	−4.3 (3)	C16—C17—C18—C19	0.3 (3)
C4—C3—C8—C9	127.1 (2)	F2—C17—C18—C19	−179.50 (19)
C2—C3—C4—C5	0.5 (3)	C17—C18—C19—C14	−0.5 (3)
C4—C3—C8—C13	−50.8 (3)	N1—C20—C21—C22	179.20 (18)
C2—C3—C8—C13	133.7 (2)	C25—C20—C21—C22	−0.1 (3)
C2—C3—C8—C9	−48.4 (3)	N1—C20—C25—C24	−179.86 (18)
C8—C3—C4—C5	−175.18 (19)	C21—C20—C25—C24	−0.6 (3)
C3—C4—C5—C6	3.0 (3)	C20—C21—C22—C23	0.7 (3)
C3—C4—C5—C14	−177.90 (19)	C21—C22—C23—C24	−0.6 (3)
C6—C5—C14—C15	−142.5 (2)	C22—C23—C24—C25	−0.1 (3)
C14—C5—C6—C7	178.28 (17)	C23—C24—C25—C20	0.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg5 is the centroid of the C20–C25 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···O1ⁱ	0.86 (2)	2.00 (2)	2.830 (2)	162 (2)
C6—H6···F1ⁱⁱ	0.93	2.49	3.362 (2)	156
C21—H21···N2	0.93	2.48	2.799 (3)	100
C25—H25···O1	0.93	2.43	2.941 (3)	115
C15—H15···Cg5ⁱⁱⁱ	0.93	2.85	3.656 (2)	145

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) x, y+1, z; (iii) x, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₁₆F₂N₂O
M_r	398.40
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	123
a, b, c (Å)	15.2947 (4), 11.6259 (2), 20.9388 (5)
V (Å³)	3723.23 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.49 × 0.38 × 0.23

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.895, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	19870, 3827, 3416
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.135, 1.09
No. of reflections	3827
No. of parameters	275
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.35

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg5 is the centroid of the C20–C25 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···O1ⁱ	0.859 (18)	2.002 (18)	2.830 (2)	162 (2)
C6—H6···F1ⁱⁱ	0.93	2.4900	3.362 (2)	156
C15—H15···Cg5ⁱⁱⁱ	0.93	2.85	3.656 (2)	145

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) x, y+1, z; (iii) x, −y, z+1/2.

Acknowledgements

SS and BN thank Mangalore University and the UGC SAP for financial assistance for the purchase of chemicals. HSY thanks the UOM for sabbatical leave.

References

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Volume 67| Part 6| June 2011| Pages o1346-o1347

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