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Acta Cryst. (2006). C62, o540-o543
https://doi.org/10.1107/S010827010602378X
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4-(4-Fluoro-3-phenoxy­phen­yl)-6-(4-fluoro­phen­yl)-2-oxo-1,2-dihydro­pyridine-3-carbonitrile and the 6-(4-methyl­phen­yl)- analogue

D. Chopra, T. P. Mohan, B. Vishalakshi and T. N. Guru Row
The crystal structures of the title compounds, viz. C24H14F2N2O2, (I), and C25H17FN2O2, (II), respectively, have been determined in order to unravel the role of an ordered F atom in generating stable supra­molecular assemblies. On changing the substitution from fluorine to a methyl group, C-H...F inter­actions are replaced by C-H...[pi] inter­actions, revealing the importance of such weak inter­actions when present alongside N-H...O and C-H...O hydrogen bonds. The dihedral angle between the planes of the 4-fluoro­phenyl ring and the pyridine ring is 26.8 (1)° in (I), while that between the planes of the 4-methyl­phenyl and pyridine rings is 29.5 (1)° in (II).
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010602378X/ob3010sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010602378X/ob3010Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010602378X/ob3010IIsup3.hkl
Contains datablock II

CCDC references: 621277; 621278

Comment top

Crystal engineering via manipulation of hydrogen bonding has gained a lot of interest in recent literature (Aakeröy, 1997; Guru Row, 1999; Desiraju, 2000, 2002; Hunter et al., 2001). Weak C—H···π interactions (Nishio et al., 1995; Umezawa et al., 1999; Takahashi et al., 2000), π stacking (Hunter, 1993, 1994) and C—H···O (Steiner, 2002) interactions have been found to generate different crystalline motifs. Organo-halo compounds also have been found to generate motifs via C—H···X, X···X and C—X···π interactions (Thalladi et al., 1998). It has been shown that fluorine does not readily accept hydrogen bonding and hence behaves differently than Cl and Br (Shimoni & Glusker, 1994; Howard et al., 1996; Dunitz & Taylor, 1997; Desiraju & Parthasarathi, 1989). Recently, the role of disordered fluorine with respect to a perfectly ordered F atom has played an important role in a stabilizing a crystalline lattice on cryo-cooling of fluorinated amines that are liquids (Chopra et al., 2006). We have been interested in the study of the role that organic fluorine plays in the packing of molecules that exhibit biological activity. Against this background, we report here the molecular and crystal structures of 4-(4-fluoro-3-phenoxyphenyl)-6-(4-fluorophenyl)- 2-oxo-1,2-dihydropyridine-3-carbonitrile, (I), and 4-(4-fluoro-3-phenoxyphenyl)-6-(4-methylphenyl)-2-oxo -1,2-dihydropyridine-3-carbonitrile, (II), in order to evaluate the importance of fluorine in the context of crystal engineering and also to study the influence of substituents of different sizes on the structural parameters of the molecule. Compounds (I) and (II) have important applications in the agrochemical industry and their biological activity has been studied (Mohan, 2006).

Figs. 1 and 2 are ORTEP-3 (Farrugia, 1997) views of the molecules of (I) and (II). Relevant bond lengths, bond angles and torsion angles are given in Tables 1 and 3. The compounds crystallize in the same triclinic space group P1 and are hence isostructural. The structures of (I) and (II) have the same molecular dimensions. The bond distances in the dihydropyridine ring A (C16/C17/C13/C14/C15/N1) are 1.360 (3)–1.434(5) Å in (I) and (II), suggesting possible resonance delocalization of the π electrons over the ring (Allen et al., 1987). Ring A is almost planar, with atoms C14 and C15 having deviation of 0.011 (4) and -0.011 (3) Å from the plane passing through C13, N1 and C17. The corresponding deviations in (II) are -0.009 (4) and +0.009 (4) Å, respectively. Steric interactions force the benzene rings out of the plane of ring A by 56.1 (1) and 26.8 (1)° for the fluorophenoxy (ring C) and fluorophenyl (ring D) groups in (I). Similar dihedral twists are observed for (II), the values being 55.4 (1) and 29.5 (1)°, respectively. The triple-bond character of the C18≡N2 bond [1.147 (3) and 1.144 (4) Å] and the C17—C18—N2 bond angle of ~179° defining the linearity of the cyano group are typical of this group of 3-cyano-2-pyridine compounds (Black et al., 1992; Hussain et al., 1996).

The supramolecular assembly in (I) is built up by a network of strong N—H···O hydrogen bonds (involving H1N and O2), forming molecular dimers (Fig. 3); these are further stabilized by C—H···O interactions (involving H24) to O2, leading to the formation of bifurcated hydrogen bonds (Jeffrey et al., 1985) that form motifs that can be described as R22(8) and R22(14) using the graph-set formalism (Bernstein et al., 1995). Weak intermolecular C—H···F interactions involving atom F2 link the molecular dimers, forming chains described by the graph-set descriptor C(18). Furthermore, π–π aromatic interactions, with a Cg3···Cg3 distance of 3.605 (3) Å (Cg3 is the centroid of ring C) provide additional stability.

In (II), replacement of a fluoro group by a methyl group leads to an identical supramolecular assembly (Fig. 4), except that the C—H···F interaction is now replaced by a C—H···π weak interaction involving atom H25C and the electron-rich 4-methylphenyl group (ring D, with centroid Cg4) acting as an electron donor, leading to formation of dimers. Such C—H···π dimers further link the molecules that are linked by N—H···O and C—H···O hydrogen bonds, forming alternating dimers built up by a cooperative interplay of strong hydrogen bonds, weak intermolecular interaction and isotropic van der Waals interactions. The Cg3···Cg3 stacking distance between rings C is 3.680 (3) Å, which is similar to the value observed in (I). In conclusion, ordered organic fluorine plays an important role in generating a stable packing motif in the crystalline lattice.#

Experimental top

The general procedure for syntheses of compounds (I) and (II) is in accordance with the literature (Dandia et al., 1996; Bhatt et al., 2001). Equimolar (0.02 mol) quantities of 4-fluoro-3-phenoxyphenyl benzaldehyde (in MeOH) were added to a mixture of 4-substituted acetophenones (X = F and methyl) in the presence of 40% NaOH (5 ml) and the mixtuer was stirred at 298 K for 24 h. The contents were poured into crushed ice and purified by recrystallization from ethanol to obtain the pure chalcone. To a mixture of this chalcone, cyanoacetamide was added in equal amount in absolute ethanol and in the presence of pyridine as a catalyst. The reaction mixture was refluxed for 4 h and then cooled, and ice-cold water was added. Pale-yellow compounds were obtained in both cases, and were purified by recrystallization from isopropyl alcohol. Crystals of (I) and (II) suitable for X-ray diffraction were grown from acetone solutions by slow evaporation at 275–277 K.

Refinement top

For both (I) and (II), the amine H atom was located from a difference Fourier map and refined isotropically. The other H atoms were placed in idealized positions (C—H = 0.93 and 0.96 Å) and constrained to ride on the parent atom, with Uiso(H) values of 1.2Ueq(C) for aromatic or 1.5Ueq(C) for methyl H atoms.

Structure description top

Crystal engineering via manipulation of hydrogen bonding has gained a lot of interest in recent literature (Aakeröy, 1997; Guru Row, 1999; Desiraju, 2000, 2002; Hunter et al., 2001). Weak C—H···π interactions (Nishio et al., 1995; Umezawa et al., 1999; Takahashi et al., 2000), π stacking (Hunter, 1993, 1994) and C—H···O (Steiner, 2002) interactions have been found to generate different crystalline motifs. Organo-halo compounds also have been found to generate motifs via C—H···X, X···X and C—X···π interactions (Thalladi et al., 1998). It has been shown that fluorine does not readily accept hydrogen bonding and hence behaves differently than Cl and Br (Shimoni & Glusker, 1994; Howard et al., 1996; Dunitz & Taylor, 1997; Desiraju & Parthasarathi, 1989). Recently, the role of disordered fluorine with respect to a perfectly ordered F atom has played an important role in a stabilizing a crystalline lattice on cryo-cooling of fluorinated amines that are liquids (Chopra et al., 2006). We have been interested in the study of the role that organic fluorine plays in the packing of molecules that exhibit biological activity. Against this background, we report here the molecular and crystal structures of 4-(4-fluoro-3-phenoxyphenyl)-6-(4-fluorophenyl)- 2-oxo-1,2-dihydropyridine-3-carbonitrile, (I), and 4-(4-fluoro-3-phenoxyphenyl)-6-(4-methylphenyl)-2-oxo -1,2-dihydropyridine-3-carbonitrile, (II), in order to evaluate the importance of fluorine in the context of crystal engineering and also to study the influence of substituents of different sizes on the structural parameters of the molecule. Compounds (I) and (II) have important applications in the agrochemical industry and their biological activity has been studied (Mohan, 2006).

Figs. 1 and 2 are ORTEP-3 (Farrugia, 1997) views of the molecules of (I) and (II). Relevant bond lengths, bond angles and torsion angles are given in Tables 1 and 3. The compounds crystallize in the same triclinic space group P1 and are hence isostructural. The structures of (I) and (II) have the same molecular dimensions. The bond distances in the dihydropyridine ring A (C16/C17/C13/C14/C15/N1) are 1.360 (3)–1.434(5) Å in (I) and (II), suggesting possible resonance delocalization of the π electrons over the ring (Allen et al., 1987). Ring A is almost planar, with atoms C14 and C15 having deviation of 0.011 (4) and -0.011 (3) Å from the plane passing through C13, N1 and C17. The corresponding deviations in (II) are -0.009 (4) and +0.009 (4) Å, respectively. Steric interactions force the benzene rings out of the plane of ring A by 56.1 (1) and 26.8 (1)° for the fluorophenoxy (ring C) and fluorophenyl (ring D) groups in (I). Similar dihedral twists are observed for (II), the values being 55.4 (1) and 29.5 (1)°, respectively. The triple-bond character of the C18≡N2 bond [1.147 (3) and 1.144 (4) Å] and the C17—C18—N2 bond angle of ~179° defining the linearity of the cyano group are typical of this group of 3-cyano-2-pyridine compounds (Black et al., 1992; Hussain et al., 1996).

The supramolecular assembly in (I) is built up by a network of strong N—H···O hydrogen bonds (involving H1N and O2), forming molecular dimers (Fig. 3); these are further stabilized by C—H···O interactions (involving H24) to O2, leading to the formation of bifurcated hydrogen bonds (Jeffrey et al., 1985) that form motifs that can be described as R22(8) and R22(14) using the graph-set formalism (Bernstein et al., 1995). Weak intermolecular C—H···F interactions involving atom F2 link the molecular dimers, forming chains described by the graph-set descriptor C(18). Furthermore, π–π aromatic interactions, with a Cg3···Cg3 distance of 3.605 (3) Å (Cg3 is the centroid of ring C) provide additional stability.

In (II), replacement of a fluoro group by a methyl group leads to an identical supramolecular assembly (Fig. 4), except that the C—H···F interaction is now replaced by a C—H···π weak interaction involving atom H25C and the electron-rich 4-methylphenyl group (ring D, with centroid Cg4) acting as an electron donor, leading to formation of dimers. Such C—H···π dimers further link the molecules that are linked by N—H···O and C—H···O hydrogen bonds, forming alternating dimers built up by a cooperative interplay of strong hydrogen bonds, weak intermolecular interaction and isotropic van der Waals interactions. The Cg3···Cg3 stacking distance between rings C is 3.680 (3) Å, which is similar to the value observed in (I). In conclusion, ordered organic fluorine plays an important role in generating a stable packing motif in the crystalline lattice.#

Computing details top

For both compounds, data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. ORTEP-3 (Farrugia, 1997) view of (I), drawn with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. ORTEP-3 view of (II), drawn with 50% probability displacement ellipsoids.
[Figure 3] Fig. 3. The packing of (I), highlighting N—H···O/C—H···O dimers and C—H···F interactions (hydrogen bonds are shown as dashed lines). Other H atoms have been omitted for clarity. The symbols ' and * on atom labels indicate symmetry-related positions at (1 - x, 1 - y, 1 - z) and (x + 1, y - 1, z - 1), respectively.
[Figure 4] Fig. 4. The packing of (II), highlighting N—H···O/C—H···O dimers (hydrogen bonds are shown as dashed lines). Other H atoms have been omitted for clarity. The symbol ' indicates the symmetry-related position at (1 - x, 1 - y, 1 - z).
(I) 4-(4-Fluoro-3-phenoxyphenyl)-6-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine- 3-carbonitrile top
Crystal data top
C24H14F2N2O2Z = 2
Mr = 400.37F(000) = 412
Triclinic, P1Dx = 1.375 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.572 (4) ÅCell parameters from 455 reflections
b = 9.337 (5) Åθ = 1.4–25.4°
c = 14.027 (8) ŵ = 0.10 mm−1
α = 80.546 (10)°T = 290 K
β = 86.710 (12)°Block, colorless
γ = 81.598 (10)°0.09 × 0.03 × 0.02 mm
V = 967.2 (9) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		3843 independent reflections
Radiation source: fine-focus sealed tube3260 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
φ and ω scansθmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.948, Tmax = 0.998k = −11→11
10089 measured reflectionsl = −17→17
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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.0358P)2]
where P = (Fo2 + 2Fc2)/3
3843 reflections(Δ/σ)max < 0.001
275 parametersΔρmax = 0.14 e Å−3
0 restraintsΔρmin = −0.15 e Å−3
Crystal data top
C24H14F2N2O2γ = 81.598 (10)°
Mr = 400.37V = 967.2 (9) Å3
Triclinic, P1Z = 2
a = 7.572 (4) ÅMo Kα radiation
b = 9.337 (5) ŵ = 0.10 mm−1
c = 14.027 (8) ÅT = 290 K
α = 80.546 (10)°0.09 × 0.03 × 0.02 mm
β = 86.710 (12)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		3843 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3260 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.998Rint = 0.073
10089 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0740 restraints
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 0.98Δρmax = 0.14 e Å−3
3843 reflectionsΔρmin = −0.15 e Å−3
275 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
F10.0527 (2)0.2506 (2)−0.08774 (13)0.0738 (6)
F2−0.3179 (3)1.0145 (2)0.54226 (15)0.1015 (8)
N10.3036 (3)0.5428 (3)0.4122 (2)0.0523 (8)
N20.6198 (4)0.2070 (3)0.2194 (2)0.0715 (10)
O10.3431 (3)0.3911 (2)−0.09495 (15)0.0604 (7)
O20.5749 (3)0.3997 (3)0.41606 (16)0.0784 (8)
C10.7055 (7)0.0562 (6)−0.1805 (5)0.115 (2)
C20.5961 (7)0.1474 (6)−0.2458 (4)0.1060 (17)
C30.4723 (5)0.2579 (4)−0.2164 (3)0.0728 (12)
C40.4616 (4)0.2728 (4)−0.1202 (3)0.0514 (9)
C50.5679 (5)0.1815 (4)−0.0543 (3)0.0693 (11)
C60.6910 (5)0.0739 (5)−0.0849 (4)0.1001 (15)
C70.2447 (4)0.3656 (3)−0.0089 (2)0.0442 (8)
C80.2858 (4)0.4143 (3)0.0731 (2)0.0466 (9)
C90.1757 (4)0.4004 (3)0.1560 (2)0.0407 (8)
C100.0199 (4)0.3384 (3)0.1546 (2)0.0510 (9)
C11−0.0208 (4)0.2870 (3)0.0732 (2)0.0552 (10)
C120.0910 (5)0.3004 (4)−0.0065 (2)0.0498 (9)
C130.2244 (4)0.4500 (3)0.2452 (2)0.0435 (8)
C140.1038 (4)0.5504 (3)0.2889 (2)0.0505 (9)
C150.1435 (4)0.5989 (3)0.3706 (2)0.0453 (9)
C160.4313 (5)0.4423 (4)0.3746 (2)0.0552 (10)
C170.3852 (4)0.3965 (3)0.2880 (2)0.0454 (9)
C180.5152 (4)0.2913 (4)0.2496 (2)0.0523 (9)
C190.0249 (4)0.7091 (3)0.4174 (2)0.0464 (9)
C20−0.0958 (4)0.8124 (4)0.3618 (2)0.0646 (11)
C21−0.2121 (4)0.9145 (4)0.4034 (3)0.0758 (12)
C22−0.2052 (5)0.9142 (4)0.5007 (3)0.0654 (11)
C23−0.0877 (5)0.8171 (4)0.5572 (2)0.0637 (11)
C240.0276 (4)0.7149 (4)0.5153 (2)0.0565 (10)
H1N0.341 (4)0.569 (4)0.469 (3)0.088 (13)*
H10.7889−0.0171−0.20070.138*
H20.60490.1352−0.31050.127*
H30.39840.3205−0.26070.087*
H50.55730.19200.01070.083*
H60.76550.0123−0.04050.120*
H80.38910.45720.07330.056*
H10−0.05700.33180.20880.061*
H11−0.12360.24350.07250.066*
H14−0.00630.58490.26140.061*
H20−0.09780.81230.29550.077*
H21−0.29340.98200.36610.091*
H23−0.08510.81970.62310.076*
H240.10870.64860.55340.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0795 (14)0.0927 (16)0.0571 (13)−0.0088 (11)−0.0195 (10)−0.0317 (12)
F20.0902 (16)0.1170 (19)0.0978 (18)0.0286 (14)−0.0049 (13)−0.0559 (15)
N10.0438 (18)0.072 (2)0.0430 (18)0.0041 (15)−0.0170 (15)−0.0201 (17)
N20.056 (2)0.080 (2)0.075 (2)0.0135 (17)−0.0077 (17)−0.0212 (18)
O10.0671 (15)0.0666 (17)0.0427 (15)0.0068 (13)0.0031 (12)−0.0105 (12)
O20.0550 (16)0.114 (2)0.0683 (17)0.0254 (14)−0.0400 (13)−0.0394 (15)
C10.106 (4)0.082 (4)0.164 (6)−0.009 (3)0.045 (4)−0.058 (4)
C20.115 (4)0.117 (5)0.104 (4)−0.039 (3)0.047 (3)−0.066 (4)
C30.084 (3)0.087 (3)0.057 (3)−0.021 (2)0.008 (2)−0.035 (2)
C40.051 (2)0.052 (3)0.054 (2)−0.0088 (19)0.0041 (19)−0.019 (2)
C50.064 (3)0.057 (3)0.082 (3)0.005 (2)0.006 (2)−0.014 (2)
C60.079 (3)0.068 (3)0.146 (5)0.007 (2)0.013 (3)−0.015 (3)
C70.048 (2)0.045 (2)0.035 (2)0.0085 (17)−0.0053 (17)−0.0068 (17)
C80.042 (2)0.057 (2)0.042 (2)−0.0009 (16)−0.0096 (17)−0.0116 (18)
C90.0370 (19)0.047 (2)0.037 (2)0.0060 (16)−0.0094 (16)−0.0104 (17)
C100.036 (2)0.070 (3)0.047 (2)0.0004 (18)−0.0065 (16)−0.0163 (19)
C110.043 (2)0.072 (3)0.056 (2)−0.0035 (18)−0.0134 (18)−0.022 (2)
C120.057 (2)0.057 (3)0.037 (2)0.0073 (19)−0.0174 (19)−0.0188 (19)
C130.0364 (19)0.055 (2)0.038 (2)0.0000 (17)−0.0052 (16)−0.0094 (17)
C140.0358 (19)0.074 (3)0.042 (2)0.0029 (18)−0.0168 (16)−0.0161 (19)
C150.037 (2)0.059 (2)0.040 (2)−0.0018 (17)−0.0086 (16)−0.0089 (18)
C160.046 (2)0.073 (3)0.048 (2)0.002 (2)−0.0134 (18)−0.017 (2)
C170.0361 (19)0.059 (2)0.041 (2)0.0034 (17)−0.0096 (15)−0.0115 (18)
C180.044 (2)0.065 (3)0.047 (2)−0.0014 (19)−0.0131 (17)−0.009 (2)
C190.043 (2)0.058 (2)0.037 (2)0.0013 (17)−0.0088 (16)−0.0111 (18)
C200.066 (2)0.079 (3)0.047 (2)0.015 (2)−0.0161 (19)−0.021 (2)
C210.074 (3)0.082 (3)0.068 (3)0.022 (2)−0.023 (2)−0.023 (2)
C220.057 (3)0.077 (3)0.066 (3)0.006 (2)−0.002 (2)−0.036 (2)
C230.059 (2)0.088 (3)0.044 (2)−0.001 (2)−0.003 (2)−0.019 (2)
C240.049 (2)0.074 (3)0.045 (2)0.0025 (19)−0.0073 (17)−0.015 (2)
Geometric parameters (Å, º) top
F1—C121.361 (3)C11—C101.377 (4)
O1—C71.387 (3)C11—H110.9300
O1—C41.398 (3)C24—C231.379 (4)
N1—C151.371 (3)C24—H240.9300
N1—C161.390 (4)C22—C231.361 (4)
N1—H1N0.94 (3)C22—C211.369 (4)
O2—C161.244 (3)C20—C211.380 (4)
C13—C171.378 (4)C20—H200.9300
C13—C141.401 (4)C10—H100.9300
C13—C91.486 (4)C8—H80.9300
F2—C221.354 (3)C4—C51.362 (4)
C19—C241.384 (4)C4—C31.376 (4)
C19—C201.397 (4)C21—H210.9300
C19—C151.476 (4)C23—H230.9300
C15—C141.364 (4)C5—C61.374 (5)
C9—C101.390 (4)C5—H50.9300
C9—C81.391 (4)C3—C21.388 (5)
C14—H140.9300C3—H30.9300
C7—C81.371 (4)C1—C21.369 (6)
C7—C121.386 (4)C1—C61.374 (6)
C16—C171.429 (4)C1—H10.9300
C12—C111.363 (4)C6—H60.9300
C18—N21.147 (3)C2—H20.9300
C18—C171.433 (4)
C7—O1—C4116.7 (2)C16—C17—C18115.9 (3)
C15—N1—C16124.1 (3)F2—C22—C23118.7 (3)
C15—N1—H1N124 (2)F2—C22—C21119.1 (4)
C16—N1—H1N112 (2)C23—C22—C21122.2 (3)
C17—C13—C14118.6 (3)C21—C20—C19121.1 (3)
C17—C13—C9121.4 (3)C21—C20—H20119.4
C14—C13—C9119.9 (3)C19—C20—H20119.4
C24—C19—C20117.9 (3)C11—C10—C9120.1 (3)
C24—C19—C15122.6 (3)C11—C10—H10119.9
C20—C19—C15119.5 (3)C9—C10—H10119.9
C14—C15—N1118.3 (3)C7—C8—C9121.1 (3)
C14—C15—C19124.1 (3)C7—C8—H8119.4
N1—C15—C19117.6 (3)C9—C8—H8119.4
C10—C9—C8119.1 (3)C5—C4—C3121.6 (3)
C10—C9—C13120.3 (3)C5—C4—O1122.0 (3)
C8—C9—C13120.5 (3)C3—C4—O1116.4 (3)
C15—C14—C13121.7 (3)C22—C21—C20118.5 (3)
C15—C14—H14119.1C22—C21—H21120.7
C13—C14—H14119.1C20—C21—H21120.7
C8—C7—C12118.0 (3)C22—C23—C24119.0 (3)
C8—C7—O1121.9 (3)C22—C23—H23120.5
C12—C7—O1119.8 (3)C24—C23—H23120.5
O2—C16—N1119.7 (3)C4—C5—C6119.2 (4)
O2—C16—C17124.7 (3)C4—C5—H5120.4
N1—C16—C17115.6 (3)C6—C5—H5120.4
F1—C12—C11120.2 (3)C4—C3—C2118.4 (4)
F1—C12—C7117.6 (3)C4—C3—H3120.8
C11—C12—C7122.2 (3)C2—C3—H3120.8
N2—C18—C17179.6 (4)C2—C1—C6119.5 (5)
C12—C11—C10119.3 (3)C2—C1—H1120.3
C12—C11—H11120.3C6—C1—H1120.3
C10—C11—H11120.3C5—C6—C1120.7 (5)
C23—C24—C19121.3 (3)C5—C6—H6119.6
C23—C24—H24119.4C1—C6—H6119.6
C19—C24—H24119.4C1—C2—C3120.6 (5)
C13—C17—C16121.6 (3)C1—C2—H2119.7
C13—C17—C18122.6 (3)C3—C2—H2119.7
C16—N1—C15—C142.0 (5)O2—C16—C17—C13−179.0 (3)
C16—N1—C15—C19−177.7 (3)N1—C16—C17—C130.2 (5)
C24—C19—C15—C14153.2 (3)O2—C16—C17—C181.6 (5)
C20—C19—C15—C14−26.7 (5)N1—C16—C17—C18−179.1 (3)
C24—C19—C15—N1−27.1 (4)C24—C19—C20—C21−1.7 (5)
C20—C19—C15—N1153.0 (3)C15—C19—C20—C21178.2 (3)
C17—C13—C9—C10123.0 (3)C12—C11—C10—C9−1.4 (5)
C14—C13—C9—C10−55.4 (4)C8—C9—C10—C112.3 (5)
C17—C13—C9—C8−56.5 (4)C13—C9—C10—C11−177.2 (3)
C14—C13—C9—C8125.1 (3)C12—C7—C8—C9−0.8 (4)
N1—C15—C14—C13−2.4 (5)O1—C7—C8—C9173.6 (3)
C19—C15—C14—C13177.3 (3)C10—C9—C8—C7−1.1 (4)
C17—C13—C14—C151.7 (5)C13—C9—C8—C7178.4 (3)
C9—C13—C14—C15−179.9 (3)C7—O1—C4—C5−43.2 (4)
C4—O1—C7—C8103.8 (3)C7—O1—C4—C3140.3 (3)
C4—O1—C7—C12−81.8 (3)F2—C22—C21—C20179.6 (3)
C15—N1—C16—O2178.3 (3)C23—C22—C21—C200.1 (6)
C15—N1—C16—C17−1.0 (5)C19—C20—C21—C221.0 (5)
C8—C7—C12—F1−179.1 (3)F2—C22—C23—C24−179.9 (3)
O1—C7—C12—F16.4 (4)C21—C22—C23—C24−0.5 (6)
C8—C7—C12—C111.7 (5)C19—C24—C23—C22−0.4 (5)
O1—C7—C12—C11−172.8 (3)C3—C4—C5—C61.2 (6)
F1—C12—C11—C10−179.8 (3)O1—C4—C5—C6−175.1 (3)
C7—C12—C11—C10−0.6 (5)C5—C4—C3—C2−0.5 (5)
C20—C19—C24—C231.4 (5)O1—C4—C3—C2176.1 (3)
C15—C19—C24—C23−178.5 (3)C4—C5—C6—C1−1.1 (6)
C14—C13—C17—C16−0.6 (5)C2—C1—C6—C50.2 (8)
C9—C13—C17—C16−179.0 (3)C6—C1—C2—C30.5 (8)
C14—C13—C17—C18178.7 (3)C4—C3—C2—C1−0.4 (7)
C9—C13—C17—C180.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.94 (4)1.85 (4)2.786 (4)175 (3)
C24—H24···O2i0.932.423.191 (4)140
C2—H2···F2ii0.932.513.399 (6)159
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y−1, z−1.
(II) 4-(4-Fluoro-3-phenoxyphenyl)-6-(4-methylphenyl)-2-oxo-1,2-dihydropyridine- 3-carbonitrile top
Crystal data top
C25H17FN2O2Z = 2
Mr = 396.41F(000) = 412
Triclinic, P1Dx = 1.310 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.828 (5) ÅCell parameters from 535 reflections
b = 9.523 (7) Åθ = 1.3–25.2°
c = 13.952 (10) ŵ = 0.09 mm−1
α = 76.460 (13)°T = 290 K
β = 87.250 (14)°Plate, colorless
γ = 83.705 (15)°0.15 × 0.14 × 0.05 mm
V = 1004.9 (12) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		3976 independent reflections
Radiation source: fine-focus sealed tube1997 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
φ and ω scansθmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.946, Tmax = 0.996k = −11→11
10474 measured reflectionsl = −17→17
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)] = 0.096Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 1.14 w = 1/[σ2(Fo2) + (0.0454P)2]
where P = (Fo2 + 2Fc2)/3
3976 reflections(Δ/σ)max < 0.001
276 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C25H17FN2O2γ = 83.705 (15)°
Mr = 396.41V = 1004.9 (12) Å3
Triclinic, P1Z = 2
a = 7.828 (5) ÅMo Kα radiation
b = 9.523 (7) ŵ = 0.09 mm−1
c = 13.952 (10) ÅT = 290 K
α = 76.460 (13)°0.15 × 0.14 × 0.05 mm
β = 87.250 (14)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		3976 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1997 reflections with I > 2σ(I)
Tmin = 0.946, Tmax = 0.996Rint = 0.067
10474 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0960 restraints
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 1.14Δρmax = 0.21 e Å−3
3976 reflectionsΔρmin = −0.18 e Å−3
276 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
F10.0592 (3)0.2500 (2)−0.08137 (16)0.0703 (7)
O10.3464 (3)0.3916 (3)−0.09466 (17)0.0555 (8)
O20.5686 (3)0.3953 (3)0.42196 (19)0.0669 (9)
N10.3120 (4)0.5362 (3)0.4080 (2)0.0448 (9)
N20.6158 (4)0.2192 (4)0.2275 (2)0.0662 (11)
C10.6814 (8)0.0630 (6)−0.1657 (5)0.101 (2)
C20.5684 (8)0.1461 (6)−0.2331 (4)0.0989 (19)
C30.4540 (6)0.2547 (5)−0.2087 (3)0.0719 (14)
C40.4560 (5)0.2744 (4)−0.1147 (3)0.0494 (11)
C50.5670 (5)0.1915 (4)−0.0459 (3)0.0651 (12)
C60.6804 (6)0.0851 (5)−0.0722 (4)0.0870 (16)
C70.2497 (5)0.3657 (4)−0.0076 (3)0.0397 (9)
C80.2930 (4)0.4139 (4)0.0724 (3)0.0403 (9)
C90.1851 (4)0.4007 (4)0.1559 (2)0.0361 (9)
C100.0316 (4)0.3409 (4)0.1557 (3)0.0446 (10)
C11−0.0109 (5)0.2882 (4)0.0768 (3)0.0501 (11)
C120.0991 (5)0.3018 (4)−0.0031 (3)0.0449 (10)
C130.2349 (4)0.4503 (4)0.2427 (2)0.0369 (9)
C140.1209 (5)0.5471 (4)0.2821 (3)0.0409 (10)
C150.1591 (4)0.5920 (4)0.3636 (3)0.0374 (9)
C160.4337 (5)0.4392 (4)0.3765 (3)0.0446 (10)
C170.3892 (4)0.3978 (4)0.2892 (3)0.0396 (9)
C180.5145 (5)0.2980 (4)0.2546 (3)0.0442 (10)
C190.0460 (4)0.6943 (4)0.4080 (3)0.0386 (9)
C20−0.0640 (5)0.8021 (4)0.3495 (3)0.0539 (11)
C21−0.1692 (5)0.9003 (4)0.3911 (3)0.0604 (12)
C22−0.1687 (5)0.8930 (4)0.4913 (3)0.0491 (10)
C23−0.0596 (5)0.7868 (4)0.5478 (3)0.0505 (11)
C240.0461 (4)0.6881 (4)0.5084 (3)0.0462 (10)
C25−0.2819 (5)0.9994 (4)0.5379 (3)0.0700 (13)
H1N0.340 (4)0.559 (4)0.461 (3)0.049 (12)*
H10.7588−0.0085−0.18330.121*
H20.56840.1294−0.29620.119*
H30.37840.3124−0.25470.086*
H50.56580.20670.01760.078*
H60.75660.0280−0.02620.104*
H80.39530.45570.07100.048*
H10−0.04390.33610.20970.054*
H11−0.11190.24460.07810.060*
H140.01590.58140.25190.049*
H20−0.06700.80830.28200.065*
H21−0.24100.97220.35100.073*
H23−0.05660.78110.61520.061*
H240.11770.61690.54920.055*
H25A−0.37820.95320.57130.105*
H25B−0.32251.08210.48760.105*
H25C−0.21681.03040.58440.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0841 (17)0.0899 (19)0.0496 (15)−0.0092 (13)−0.0182 (13)−0.0381 (14)
O10.0791 (19)0.0535 (18)0.0331 (16)0.0012 (14)0.0071 (14)−0.0136 (13)
O20.0550 (17)0.092 (2)0.0639 (19)0.0278 (16)−0.0343 (15)−0.0478 (17)
N10.050 (2)0.056 (2)0.034 (2)0.0026 (16)−0.0127 (17)−0.0228 (18)
N20.061 (2)0.077 (3)0.062 (3)0.018 (2)−0.0062 (19)−0.028 (2)
C10.092 (4)0.079 (4)0.140 (6)−0.005 (3)0.044 (4)−0.051 (4)
C20.115 (5)0.111 (5)0.091 (5)−0.027 (4)0.042 (4)−0.066 (4)
C30.084 (3)0.088 (4)0.056 (3)−0.017 (3)0.013 (3)−0.042 (3)
C40.057 (3)0.051 (3)0.047 (3)−0.011 (2)0.009 (2)−0.023 (2)
C50.071 (3)0.059 (3)0.067 (3)0.002 (2)0.001 (3)−0.023 (3)
C60.072 (3)0.074 (4)0.113 (5)0.000 (3)0.012 (3)−0.024 (3)
C70.051 (2)0.041 (2)0.027 (2)0.0041 (19)−0.0050 (19)−0.0118 (19)
C80.043 (2)0.041 (2)0.040 (2)−0.0020 (17)−0.0049 (19)−0.0139 (19)
C90.036 (2)0.039 (2)0.035 (2)0.0063 (17)−0.0058 (18)−0.0153 (18)
C100.036 (2)0.063 (3)0.037 (2)0.0005 (19)−0.0045 (18)−0.017 (2)
C110.043 (2)0.066 (3)0.047 (3)−0.006 (2)−0.013 (2)−0.023 (2)
C120.060 (3)0.052 (3)0.027 (2)0.004 (2)−0.017 (2)−0.020 (2)
C130.041 (2)0.042 (2)0.028 (2)−0.0019 (18)−0.0055 (17)−0.0100 (18)
C140.035 (2)0.053 (3)0.037 (2)0.0025 (19)−0.0125 (18)−0.016 (2)
C150.040 (2)0.045 (2)0.029 (2)0.0013 (18)−0.0095 (17)−0.0121 (19)
C160.045 (2)0.050 (3)0.043 (3)0.0058 (19)−0.012 (2)−0.022 (2)
C170.039 (2)0.050 (2)0.035 (2)0.0019 (18)−0.0038 (17)−0.0210 (19)
C180.044 (2)0.054 (3)0.037 (2)−0.002 (2)−0.0115 (18)−0.014 (2)
C190.039 (2)0.044 (2)0.036 (2)−0.0007 (18)−0.0036 (18)−0.0177 (19)
C200.060 (3)0.061 (3)0.041 (2)0.013 (2)−0.015 (2)−0.018 (2)
C210.054 (3)0.063 (3)0.063 (3)0.019 (2)−0.018 (2)−0.020 (2)
C220.047 (2)0.048 (3)0.059 (3)−0.003 (2)0.003 (2)−0.026 (2)
C230.054 (2)0.059 (3)0.041 (2)−0.002 (2)−0.001 (2)−0.019 (2)
C240.047 (2)0.053 (3)0.037 (2)0.0025 (19)−0.0040 (19)−0.012 (2)
C250.060 (3)0.077 (3)0.080 (3)0.005 (2)0.009 (2)−0.039 (3)
Geometric parameters (Å, º) top
F1—C121.360 (4)C11—H110.9300
O1—C71.386 (4)C8—H80.9300
O1—C41.404 (4)C23—C221.370 (5)
O2—C161.239 (4)C23—C241.378 (5)
N1—C151.370 (4)C23—H230.9300
N1—C161.383 (4)C20—C211.389 (5)
N1—H1N0.86 (3)C20—H200.9300
C14—C151.362 (5)C24—H240.9300
C14—C131.399 (4)C22—C211.384 (5)
C14—H140.9300C22—C251.514 (5)
C15—C191.469 (4)C25—H25A0.9600
C16—C171.434 (5)C25—H25B0.9600
C13—C171.386 (4)C25—H25C0.9600
C13—C91.482 (4)C4—C51.369 (5)
C9—C101.386 (5)C4—C31.369 (5)
C9—C81.395 (4)C21—H210.9300
C7—C81.372 (4)C6—C11.368 (7)
C7—C121.377 (5)C6—C51.376 (5)
C19—C241.388 (5)C6—H60.9300
C19—C201.394 (4)C3—C21.386 (6)
C18—N21.144 (4)C3—H30.9300
C18—C171.436 (5)C5—H50.9300
C10—C111.380 (5)C2—C11.368 (7)
C10—H100.9300C2—H20.9300
C11—C121.367 (5)C1—H10.9300
C7—O1—C4117.0 (3)C16—C17—C18115.3 (3)
C15—N1—C16125.7 (3)C22—C23—C24122.3 (4)
C15—N1—H1N121 (2)C22—C23—H23118.8
C16—N1—H1N113 (2)C24—C23—H23118.8
C15—C14—C13121.7 (3)C21—C20—C19120.5 (4)
C15—C14—H14119.3C21—C20—H20119.8
C13—C14—H14119.3C19—C20—H20119.8
C14—C15—N1117.8 (3)C23—C24—C19120.3 (4)
C14—C15—C19124.3 (3)C23—C24—H24119.9
N1—C15—C19117.9 (3)C19—C24—H24119.9
O2—C16—N1120.7 (3)C23—C22—C21117.7 (3)
O2—C16—C17124.9 (3)C23—C22—C25120.4 (4)
N1—C16—C17114.4 (3)C21—C22—C25121.8 (4)
C17—C13—C14118.7 (3)C22—C25—H25A109.5
C17—C13—C9121.5 (3)C22—C25—H25B109.5
C14—C13—C9119.7 (3)H25A—C25—H25B109.5
C10—C9—C8118.8 (3)C22—C25—H25C109.5
C10—C9—C13121.0 (3)H25A—C25—H25C109.5
C8—C9—C13120.2 (3)H25B—C25—H25C109.5
C8—C7—C12118.6 (3)C5—C4—C3122.1 (4)
C8—C7—O1121.2 (4)C5—C4—O1121.6 (4)
C12—C7—O1119.9 (3)C3—C4—O1116.2 (4)
C24—C19—C20118.1 (3)C22—C21—C20121.1 (4)
C24—C19—C15121.5 (3)C22—C21—H21119.5
C20—C19—C15120.4 (3)C20—C21—H21119.5
N2—C18—C17179.2 (4)C1—C6—C5120.3 (5)
C11—C10—C9121.0 (3)C1—C6—H6119.9
C11—C10—H10119.5C5—C6—H6119.9
C9—C10—H10119.5C4—C3—C2117.9 (5)
C12—C11—C10118.3 (4)C4—C3—H3121.1
C12—C11—H11120.8C2—C3—H3121.1
C10—C11—H11120.8C4—C5—C6119.0 (5)
F1—C12—C11119.0 (4)C4—C5—H5120.5
F1—C12—C7118.5 (3)C6—C5—H5120.5
C11—C12—C7122.5 (4)C1—C2—C3120.9 (5)
C7—C8—C9120.6 (4)C1—C2—H2119.6
C7—C8—H8119.7C3—C2—H2119.6
C9—C8—H8119.7C2—C1—C6119.9 (5)
C13—C17—C16121.7 (3)C2—C1—H1120.0
C13—C17—C18123.0 (3)C6—C1—H1120.0
C13—C14—C15—N1−1.7 (6)C13—C9—C8—C7178.7 (3)
C13—C14—C15—C19179.4 (3)C14—C13—C17—C160.5 (5)
C16—N1—C15—C141.1 (6)C9—C13—C17—C16−176.4 (3)
C16—N1—C15—C19−179.9 (3)C14—C13—C17—C18179.9 (3)
C15—N1—C16—O2179.8 (4)C9—C13—C17—C183.0 (5)
C15—N1—C16—C170.2 (5)O2—C16—C17—C13179.4 (4)
C15—C14—C13—C171.0 (5)N1—C16—C17—C13−1.1 (5)
C15—C14—C13—C9178.0 (3)O2—C16—C17—C18−0.1 (6)
C17—C13—C9—C10124.0 (4)N1—C16—C17—C18179.5 (3)
C14—C13—C9—C10−52.9 (5)C24—C19—C20—C210.3 (6)
C17—C13—C9—C8−56.1 (5)C15—C19—C20—C21−179.0 (3)
C14—C13—C9—C8127.0 (4)C22—C23—C24—C190.6 (6)
C4—O1—C7—C8104.1 (4)C20—C19—C24—C23−0.3 (5)
C4—O1—C7—C12−81.7 (4)C15—C19—C24—C23179.0 (3)
C14—C15—C19—C24150.1 (4)C24—C23—C22—C21−0.8 (6)
N1—C15—C19—C24−28.8 (5)C24—C23—C22—C25−179.8 (3)
C14—C15—C19—C20−30.6 (6)C7—O1—C4—C5−49.6 (5)
N1—C15—C19—C20150.5 (4)C7—O1—C4—C3134.9 (4)
C8—C9—C10—C113.2 (5)C23—C22—C21—C200.8 (6)
C13—C9—C10—C11−176.8 (3)C25—C22—C21—C20179.8 (4)
C9—C10—C11—C12−2.6 (5)C19—C20—C21—C22−0.6 (6)
C10—C11—C12—F1179.8 (3)C5—C4—C3—C20.4 (6)
C10—C11—C12—C70.1 (5)O1—C4—C3—C2175.9 (4)
C8—C7—C12—F1−178.0 (3)C3—C4—C5—C60.1 (6)
O1—C7—C12—F17.7 (5)O1—C4—C5—C6−175.1 (4)
C8—C7—C12—C111.8 (5)C1—C6—C5—C4−0.1 (7)
O1—C7—C12—C11−172.6 (3)C4—C3—C2—C1−1.0 (8)
C12—C7—C8—C9−1.1 (5)C3—C2—C1—C61.1 (9)
O1—C7—C8—C9173.2 (3)C5—C6—C1—C2−0.5 (8)
C10—C9—C8—C7−1.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.86 (4)1.97 (4)2.828 (5)174 (3)
C24—H24···O2i0.932.493.173 (5)130
C25—H25C···Cg4ii0.962.853.535 (5)130
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1.

Experimental details

(I)(II)
Crystal data
Chemical formulaC24H14F2N2O2C25H17FN2O2
Mr400.37396.41
Crystal system, space groupTriclinic, P1Triclinic, P1
Temperature (K)290290
a, b, c (Å)7.572 (4), 9.337 (5), 14.027 (8)7.828 (5), 9.523 (7), 13.952 (10)
α, β, γ (°)80.546 (10), 86.710 (12), 81.598 (10)76.460 (13), 87.250 (14), 83.705 (15)
V (Å3)967.2 (9)1004.9 (12)
Z22
Radiation typeMo KαMo Kα
µ (mm−1)0.100.09
Crystal size (mm)0.09 × 0.03 × 0.020.15 × 0.14 × 0.05
Data collection
DiffractometerBruker SMART APEX CCD area-detectorBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)		Multi-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.948, 0.9980.946, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections		10089, 3843, 3260 10474, 3976, 1997
Rint0.0730.067
(sin θ/λ)max (Å−1)0.6250.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.121, 0.98 0.096, 0.159, 1.14
No. of reflections38433976
No. of parameters275276
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.14, −0.150.21, −0.18

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) for (I) top
F1—C121.361 (3)C13—C171.378 (4)
O1—C71.387 (3)C13—C141.401 (4)
N1—C151.371 (3)F2—C221.354 (3)
N1—C161.390 (4)C15—C141.364 (4)
O2—C161.244 (3)C18—N21.147 (3)
C15—N1—C16124.1 (3)N2—C18—C17179.6 (4)
C14—C15—N1118.3 (3)
C24—C19—C15—C14153.2 (3)C4—O1—C7—C8103.8 (3)
C14—C13—C9—C8125.1 (3)C7—O1—C4—C3140.3 (3)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.94 (4)1.85 (4)2.786 (4)175 (3)
C24—H24···O2i0.932.423.191 (4)140
C2—H2···F2ii0.932.513.399 (6)159
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y−1, z−1.
Selected geometric parameters (Å, º) for (II) top
F1—C121.360 (4)C14—C151.362 (5)
O1—C71.386 (4)C14—C131.399 (4)
O2—C161.239 (4)C16—C171.434 (5)
N1—C151.370 (4)C13—C171.386 (4)
N1—C161.383 (4)C18—N21.144 (4)
C15—N1—C16125.7 (3)N2—C18—C17179.2 (4)
C14—C15—N1117.8 (3)
C14—C13—C9—C8127.0 (4)C14—C15—C19—C24150.1 (4)
C4—O1—C7—C8104.1 (4)C7—O1—C4—C3134.9 (4)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.86 (4)1.97 (4)2.828 (5)174 (3)
C24—H24···O2i0.932.493.173 (5)130
C25—H25C···Cg4ii0.962.853.535 (5)130
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1.
 

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