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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2922
https://doi.org/10.1107/S160053681203783X

5-[(4-Fluoro­anilino)meth­yl]-6-methyl-N-(4-methyl­phen­yl)-2-phenyl­pyrimidin-4-amine

Jerzy Cieplik,a Marcin Stolarczyk,a Iwona Bryndalb,c* and Tadeusz Lisb

aDepartment of Organic Chemistry, Medical Academy, 9 Grodzka St, 50-137 Wrocław, Poland, bFaculty of Chemistry, University of Wrocław, 14 Joliot-Curie St, 50-383 Wrocław, Poland, and cDepartment of Bioorganic Chemistry, Faculty of Engineering and Economics, Wrocław University of Economics, 118/120 Komandorska St, 53-345 Wrocław, Poland
*Correspondence e-mail: isai@o2.pl

(Received 27 August 2012; accepted 3 September 2012; online 12 September 2012)

In the title compound, C25H23FN4, the pyrimidine ring makes dihedral angles of 11.3 (2), 24.5 (2) and 70.1 (2)° with the phenyl and two benzene rings, and the mol­ecular conformation is stabilized by an intra­molecular N—H⋯N hydrogen bond with an S(6) ring motif. In the crystal, a pair of weak C—H⋯F hydrogen bonds link two mol­ecules into an inversion dimer with an R22(16) motif. In the dimer, there is also an inter­molecular π–π stacking inter­action [centroid–centroid distance = 3.708 (4) Å] between the fluorinated benzene rings. The dimers are further linked by a C—H⋯π inter­action, so forming a column along the c axis.

Related literature

For the anti­bacterial activity of 6-methyl-2-phenyl-5-substituted pyrimidine derivatives, see: Cieplik et al. (2003[Cieplik, J., Pluta, J. & Gubrynowicz, O. (2003). Boll. Chim. Farm. 142, 146-150.], 2008[Cieplik, J., Raginia, M., Pluta, J., Gubrynowicz, O., Bryndal, I. & Lis, T. (2008). Acta Pol. Pharm. Drug Res. 65, 427-434.]); Cieplik, Stolarczyk et al. (2011[Cieplik, J., Stolarczyk, M., Pluta, J., Gubrynowicz, O., Bryndal, I., Lis, T. & Mikulewicz, M. (2011). Acta Pol. Pharm. Drug Res. 68, 57-65.]). For related structures, see: Cieplik et al. (2006[Cieplik, J., Pluta, J., Bryndal, I. & Lis, T. (2006). Acta Cryst. C62, o259-o261.], 2012[Cieplik, J., Stolarczyk, M., Bryndal, I. & Lis, T. (2012). Acta Cryst. E68, o1729-o1730.]); Cieplik, Pluta et al. (2011[Cieplik, J., Pluta, J., Bryndal, I. & Lis, T. (2011). Acta Cryst. E67, o3162.]).

[Scheme 1]

Experimental

Crystal data

  • C25H23FN4

  • Mr = 398.47

  • Triclinic, [P \overline 1]

  • a = 8.306 (4) Å

  • b = 10.070 (4) Å

  • c = 12.234 (5) Å

  • α = 88.78 (4)°

  • β = 89.12 (4)°

  • γ = 82.75 (5)°

  • V = 1014.8 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 85 K

  • 0.36 × 0.18 × 0.14 mm
Data collection

  • Oxford Xcalibur PX diffractometer with Onyx CCD

  • 17245 measured reflections

  • 8461 independent reflections

  • 4334 reflections with I > 2σ(I)

  • Rint = 0.033
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.093

  • S = 1.00

  • 8461 reflections

  • 279 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C2/N3/C4–C6 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N4—H4⋯N5 0.869 (11) 2.294 (11) 2.9820 (18) 136.2 (9)
C57—H571⋯F5i 0.99 2.54 3.440 (2) 151
C57—H572⋯Cg1ii 0.99 2.60 3.467 (7) 147
Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.]); 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681203783X/is5187sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203783X/is5187Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681203783X/is5187Isup3.cml

checkCIF report


Comment top

The pyrimidine core attracts attention as natural products and pharmacologically active compounds. In our ongoing research on an immunomodulating agent, we have synthesized some of 6-methyl-2-phenyl-5-substituted pyrimidine derivatives and their antibacterial and antifungal activities have been reported (Cieplik et al., 2003, 2008; Cieplik, Stolarczyk et al., 2011). As part of our study, we previously characterized structures of polymorphic forms of N-(4-chlorophenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine (Cieplik et al., 2006) and N-(2-fluorophenyl)-5-[(4-alloxyphenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amines (Cieplik, Pluta et al., 2011; Cieplik et al., 2012). In the continuation of our search for more potent antibacterial agent, the title compound, 5-[(4-fluoroanilino)methyl]-6-methyl-2-N-(4-methylphenyl)-phenylpyrimidin-4-amine, was also prepared.

The title compound crystallizes in P1 space group, with one molecule in the asymmetric unit (Fig. 1). There is an intramolecular N—H···N hydrogen bond between N4—H4 and N5, which closes a six-membered ring (Table 1). The N4···N5 distance [2.982 (2) Å] is longer than its conterparts in other similar compound (Cieplik, Pluta et al., 2011; Cieplik, Stolarczyk et al., 2011), compared with 2.940 (3) Å for the polymorphic form of N-(4-chlorophenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine (denoted as Ia, Cieplik et al., 2006). The conformation of the title molecule is best defined by dihedral angles formed between the pyrimidine ring and the planes of the phenyl ring attached to atom C2 and two other aryl rings of the (4-methylphenyl)amino and the (4-fluorophenyl)aminomethyl groups attached, respectively, to atoms C4 and C5 of the pyrimidine ring. These dihedral angles are 11.3 (2), 24.5 (2) and 70.1 (2)°, respectively.

The N—H···N hydrogen bonds involving the amine atom N5 as a donor are commonly observed in previously described structures (Cieplik et al., 2006, 2012; Cieplik, Pluta et al., 2011). However, in the structure of the title compound, atom H5 is not involved in any interactions. The crystal structure of the title compound is stabilized by weak C—H···F, C—H···π and π–π stacking interactions. The molecules are linked by a C—H···F interaction involving atom C57 as a donor and atom F5 (-x, -y + 1, -z + 2) as an acceptor. This results in the formation of an inversion dimer with an R22(16) ring motif. Between aryl rings of (4-fluorophenyl)aminomethyl groups of molecules forming the dimer there is also an aromatic π–π stacking interaction. The distance between the centroids of C51–C56 ring at (x, y, z) and (-x, -y + 1, -z + 2) is 3.708 (4) Å, and the interplanar spacing and the centroid offset are 3.429 (4) Å and 1.41 Å, respectively. Additionally, the C57—H572 group acts as a donor of C—H···π(arene) interaction to the pyrimidine N1/C2/N3/C4–C6 ring (-x, -y + 1, -z + 1). The combination of C—H···F and C—H···π interactions generates a column running along the [001] direction (Fig. 2).

Related literature top

For the antibacterial activity of 6-methyl-2-phenyl-5-substituted pyrimidine derivatives, see: Cieplik et al. (2003, 2008); Cieplik, Stolarczyk et al. (2011). For related structures, see: Cieplik et al. (2006, 2012); Cieplik, Pluta et al. (2011).

Experimental top

The title compound was obtained by adopting the procedure described previously by Cieplik et al. (2003). 4 g (0.0125 mmol) of 5-(chloromethyl)-6-methyl-N-(4-methylphenyl)-2-phenylpyrimidin-4-amine was dissolved in 50 ml of chloroform, and 2 g of 4-fluoroaniline was added. The reaction mixture was refluxed for 4 h with vigorous stirring, then was cooled and poured into 100 ml of water. The aqueous solution was extracted three times with chloroform (50 ml). The combined chloroform phases were dried over MgSO4, filtered and concentrated under vacuum. The oily residue was purified by column chromatography on silica gel (200–400 mesh) using CHCl3 as the eluent and by crystallization from methanol to give single crystals (yield: 3.74 g, 76.0%, m.p. 423–425 K).

Refinement top

The N-bonded H atoms were found in a difference Fourier map and their positions were refined with Uiso(H) = 1.2Ueq(N). The remaining H atoms were treated as riding on their carrier atoms, with C—H distances in the range 0.95–0.99 Å, and with Uiso(H) = 1.2Ueq(C), except methyl groups where Uiso(H) = 1.5Ueq(C).

Structure description top

The pyrimidine core attracts attention as natural products and pharmacologically active compounds. In our ongoing research on an immunomodulating agent, we have synthesized some of 6-methyl-2-phenyl-5-substituted pyrimidine derivatives and their antibacterial and antifungal activities have been reported (Cieplik et al., 2003, 2008; Cieplik, Stolarczyk et al., 2011). As part of our study, we previously characterized structures of polymorphic forms of N-(4-chlorophenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine (Cieplik et al., 2006) and N-(2-fluorophenyl)-5-[(4-alloxyphenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amines (Cieplik, Pluta et al., 2011; Cieplik et al., 2012). In the continuation of our search for more potent antibacterial agent, the title compound, 5-[(4-fluoroanilino)methyl]-6-methyl-2-N-(4-methylphenyl)-phenylpyrimidin-4-amine, was also prepared.

The title compound crystallizes in P1 space group, with one molecule in the asymmetric unit (Fig. 1). There is an intramolecular N—H···N hydrogen bond between N4—H4 and N5, which closes a six-membered ring (Table 1). The N4···N5 distance [2.982 (2) Å] is longer than its conterparts in other similar compound (Cieplik, Pluta et al., 2011; Cieplik, Stolarczyk et al., 2011), compared with 2.940 (3) Å for the polymorphic form of N-(4-chlorophenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine (denoted as Ia, Cieplik et al., 2006). The conformation of the title molecule is best defined by dihedral angles formed between the pyrimidine ring and the planes of the phenyl ring attached to atom C2 and two other aryl rings of the (4-methylphenyl)amino and the (4-fluorophenyl)aminomethyl groups attached, respectively, to atoms C4 and C5 of the pyrimidine ring. These dihedral angles are 11.3 (2), 24.5 (2) and 70.1 (2)°, respectively.

The N—H···N hydrogen bonds involving the amine atom N5 as a donor are commonly observed in previously described structures (Cieplik et al., 2006, 2012; Cieplik, Pluta et al., 2011). However, in the structure of the title compound, atom H5 is not involved in any interactions. The crystal structure of the title compound is stabilized by weak C—H···F, C—H···π and π–π stacking interactions. The molecules are linked by a C—H···F interaction involving atom C57 as a donor and atom F5 (-x, -y + 1, -z + 2) as an acceptor. This results in the formation of an inversion dimer with an R22(16) ring motif. Between aryl rings of (4-fluorophenyl)aminomethyl groups of molecules forming the dimer there is also an aromatic π–π stacking interaction. The distance between the centroids of C51–C56 ring at (x, y, z) and (-x, -y + 1, -z + 2) is 3.708 (4) Å, and the interplanar spacing and the centroid offset are 3.429 (4) Å and 1.41 Å, respectively. Additionally, the C57—H572 group acts as a donor of C—H···π(arene) interaction to the pyrimidine N1/C2/N3/C4–C6 ring (-x, -y + 1, -z + 1). The combination of C—H···F and C—H···π interactions generates a column running along the [001] direction (Fig. 2).

For the antibacterial activity of 6-methyl-2-phenyl-5-substituted pyrimidine derivatives, see: Cieplik et al. (2003, 2008); Cieplik, Stolarczyk et al. (2011). For related structures, see: Cieplik et al. (2006, 2012); Cieplik, Pluta et al. (2011).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecule of title compound, showing the atom-numbering scheme. Displacements ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dotted line indicates the intramolecular N—H···N hydrogen bond.
[Figure 2] Fig. 2. Part of the crystal structure of title compound, showing the intermolecular C—H···F, C—H···π (dashed lines) and π–π stacking interactions (double dashed lines). Dotted lines indicate intramolecular N—H···N interactions. H atoms not involved in hydrogen bonding have been omitted for clarity.
5-[(4-Fluoroanilino)methyl]-6-methyl-N-(4-methylphenyl)-2-phenylpyrimidin-4-amine top
Crystal data top
C25H23FN4Z = 2
Mr = 398.47F(000) = 420
Triclinic, P1Dx = 1.304 Mg m−3
Hall symbol: -P 1Melting point: 424 K
a = 8.306 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.070 (4) ÅCell parameters from 9708 reflections
c = 12.234 (5) Åθ = 4.8–35.0°
α = 88.78 (4)°µ = 0.09 mm−1
β = 89.12 (4)°T = 85 K
γ = 82.75 (5)°Needle block, light yellow
V = 1014.8 (8) Å30.36 × 0.18 × 0.14 mm
Data collection top
Oxford Xcalibur PX
diffractometer with Onyx CCD		4334 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 35.0°, θmin = 4.8°
φ and ω scansh = −11→13
17245 measured reflectionsk = −15→16
8461 independent reflectionsl = −19→19
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.030P)2]
where P = (Fo2 + 2Fc2)/3
8461 reflections(Δ/σ)max = 0.001
279 parametersΔρmax = 0.38 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Crystal data top
C25H23FN4γ = 82.75 (5)°
Mr = 398.47V = 1014.8 (8) Å3
Triclinic, P1Z = 2
a = 8.306 (4) ÅMo Kα radiation
b = 10.070 (4) ŵ = 0.09 mm−1
c = 12.234 (5) ÅT = 85 K
α = 88.78 (4)°0.36 × 0.18 × 0.14 mm
β = 89.12 (4)°
Data collection top
Oxford Xcalibur PX
diffractometer with Onyx CCD		4334 reflections with I > 2σ(I)
17245 measured reflectionsRint = 0.033
8461 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.38 e Å−3
8461 reflectionsΔρmin = −0.31 e Å−3
279 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
N10.10445 (10)0.79035 (8)0.41851 (7)0.01576 (19)
C20.20919 (12)0.71729 (10)0.35266 (8)0.0140 (2)
C210.25288 (12)0.78216 (10)0.24794 (8)0.0146 (2)
C220.16726 (13)0.90318 (10)0.21321 (9)0.0202 (2)
H220.07950.94410.25650.024*
C230.20876 (14)0.96450 (11)0.11618 (9)0.0249 (3)
H230.14881.04660.09300.030*
C240.33733 (13)0.90659 (11)0.05289 (9)0.0232 (3)
H240.36510.9485−0.01390.028*
C250.42520 (13)0.78748 (11)0.08714 (9)0.0223 (2)
H250.51440.74820.04430.027*
C260.38325 (13)0.72516 (10)0.18414 (8)0.0185 (2)
H260.44380.64320.20710.022*
N30.28386 (10)0.59329 (8)0.37320 (7)0.01478 (18)
C40.25062 (12)0.53878 (10)0.47043 (8)0.0142 (2)
N40.32494 (10)0.41352 (8)0.49809 (7)0.01661 (19)
H40.3281 (13)0.3965 (11)0.5680 (9)0.020*
C410.42036 (12)0.31806 (10)0.43411 (8)0.0152 (2)
C420.50900 (12)0.21177 (10)0.49004 (9)0.0173 (2)
H420.50580.20870.56770.021*
C430.60151 (12)0.11080 (10)0.43404 (9)0.0191 (2)
H430.66280.04060.47410.023*
C440.60703 (12)0.10953 (10)0.32041 (9)0.0197 (2)
C470.70423 (14)−0.00354 (12)0.26030 (10)0.0290 (3)
H4730.7735−0.05920.31200.043*
H4720.77210.03330.20400.043*
H4710.6303−0.05820.22590.043*
C450.51525 (13)0.21488 (10)0.26533 (9)0.0207 (2)
H450.51530.21580.18770.025*
C460.42383 (12)0.31843 (10)0.31983 (8)0.0183 (2)
H460.36380.38930.27970.022*
C50.14131 (12)0.60620 (10)0.54702 (8)0.0146 (2)
C570.09810 (12)0.53600 (11)0.65109 (8)0.0181 (2)
H5710.00990.59260.68970.022*
H5720.05780.45070.63320.022*
N50.23857 (11)0.50820 (9)0.72329 (7)0.0198 (2)
H50.2891 (13)0.5843 (11)0.7280 (9)0.024*
C510.20720 (12)0.45585 (10)0.82908 (8)0.0171 (2)
C520.11769 (13)0.34826 (11)0.84171 (9)0.0210 (2)
H520.07750.30990.77900.025*
C530.08662 (13)0.29654 (11)0.94486 (9)0.0215 (2)
H530.02450.22390.95350.026*
F50.11487 (8)0.30347 (6)1.13620 (5)0.02904 (17)
C540.14766 (13)0.35259 (10)1.03413 (8)0.0197 (2)
C550.23850 (13)0.45671 (11)1.02485 (9)0.0228 (2)
H550.28080.49271.08800.027*
C560.26771 (13)0.50879 (11)0.92156 (9)0.0215 (2)
H560.32980.58150.91400.026*
C60.07285 (12)0.73425 (10)0.51736 (8)0.0154 (2)
C61−0.03893 (13)0.82245 (11)0.59100 (9)0.0211 (2)
H611−0.14950.79920.58550.032*
H612−0.03750.91640.56870.032*
H613−0.00250.80930.66670.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0161 (4)0.0172 (4)0.0143 (4)−0.0035 (3)0.0008 (4)0.0001 (4)
C20.0141 (5)0.0158 (5)0.0124 (5)−0.0035 (4)−0.0012 (4)0.0000 (4)
C210.0174 (5)0.0145 (5)0.0125 (5)−0.0040 (4)−0.0001 (4)−0.0001 (4)
C220.0250 (6)0.0162 (5)0.0187 (6)0.0000 (4)0.0028 (5)0.0003 (4)
C230.0348 (7)0.0175 (6)0.0213 (6)0.0001 (5)0.0004 (5)0.0055 (5)
C240.0314 (7)0.0247 (6)0.0150 (6)−0.0107 (5)0.0014 (5)0.0041 (5)
C250.0221 (6)0.0271 (6)0.0177 (6)−0.0042 (5)0.0058 (5)0.0010 (5)
C260.0199 (6)0.0186 (5)0.0162 (5)−0.0006 (4)0.0014 (4)0.0017 (4)
N30.0156 (4)0.0157 (4)0.0135 (4)−0.0038 (3)0.0003 (3)0.0012 (3)
C40.0147 (5)0.0149 (5)0.0138 (5)−0.0042 (4)−0.0007 (4)−0.0001 (4)
N40.0215 (5)0.0166 (5)0.0109 (4)0.0002 (4)0.0017 (4)0.0023 (4)
C410.0152 (5)0.0138 (5)0.0169 (5)−0.0040 (4)0.0016 (4)0.0005 (4)
C420.0192 (5)0.0178 (5)0.0156 (5)−0.0052 (4)−0.0016 (4)0.0012 (4)
C430.0176 (5)0.0160 (5)0.0236 (6)−0.0022 (4)−0.0036 (5)0.0017 (4)
C440.0181 (5)0.0182 (5)0.0234 (6)−0.0042 (4)0.0015 (5)−0.0026 (5)
C470.0305 (7)0.0249 (6)0.0308 (7)0.0006 (5)−0.0008 (5)−0.0067 (5)
C450.0249 (6)0.0218 (6)0.0159 (6)−0.0048 (5)0.0018 (5)−0.0018 (4)
C460.0210 (6)0.0180 (5)0.0156 (5)−0.0016 (4)−0.0014 (4)0.0028 (4)
C50.0149 (5)0.0180 (5)0.0115 (5)−0.0040 (4)0.0002 (4)0.0008 (4)
C570.0190 (6)0.0212 (5)0.0137 (5)−0.0020 (4)0.0031 (4)0.0019 (4)
N50.0186 (5)0.0262 (5)0.0154 (5)−0.0067 (4)−0.0006 (4)0.0043 (4)
C510.0148 (5)0.0206 (5)0.0148 (5)0.0018 (4)0.0020 (4)0.0033 (4)
C520.0225 (6)0.0257 (6)0.0151 (6)−0.0042 (5)−0.0026 (5)0.0000 (5)
C530.0222 (6)0.0212 (6)0.0210 (6)−0.0032 (4)0.0015 (5)0.0044 (5)
F50.0398 (4)0.0301 (4)0.0151 (3)0.0018 (3)0.0043 (3)0.0068 (3)
C540.0239 (6)0.0205 (6)0.0122 (5)0.0055 (4)0.0039 (4)0.0053 (4)
C550.0299 (6)0.0221 (6)0.0155 (6)0.0007 (5)−0.0028 (5)−0.0020 (5)
C560.0243 (6)0.0195 (6)0.0209 (6)−0.0030 (4)0.0002 (5)0.0000 (5)
C60.0137 (5)0.0188 (5)0.0140 (5)−0.0035 (4)0.0001 (4)−0.0011 (4)
C610.0224 (6)0.0212 (6)0.0190 (6)−0.0009 (4)0.0057 (5)−0.0012 (4)
Geometric parameters (Å, º) top
N1—C21.3377 (14)C47—H4730.9800
N1—C61.3598 (14)C47—H4720.9800
C2—N31.3427 (14)C47—H4710.9800
C2—C211.4865 (15)C45—C461.3867 (16)
C21—C221.3928 (16)C45—H450.9500
C21—C261.3955 (16)C46—H460.9500
C22—C231.3853 (16)C5—C61.3853 (15)
C22—H220.9500C5—C571.5037 (15)
C23—C241.3845 (17)C57—N51.4692 (15)
C23—H230.9500C57—H5710.9900
C24—C251.3835 (16)C57—H5720.9900
C24—H240.9500N5—C511.4199 (14)
C25—C261.3908 (15)N5—H50.922 (11)
C25—H250.9500C51—C561.3884 (16)
C26—H260.9500C51—C521.3940 (16)
N3—C41.3389 (13)C52—C531.3879 (15)
C4—N41.3705 (14)C52—H520.9500
C4—C51.4173 (15)C53—C541.3726 (17)
N4—C411.4091 (15)C53—H530.9500
N4—H40.869 (11)F5—C541.3694 (13)
C41—C421.3932 (15)C54—C551.3688 (16)
C41—C461.3980 (15)C55—C561.3876 (16)
C42—C431.3820 (16)C55—H550.9500
C42—H420.9500C56—H560.9500
C43—C441.3905 (16)C6—C611.5043 (16)
C43—H430.9500C61—H6110.9800
C44—C451.3935 (16)C61—H6120.9800
C44—C471.5081 (17)C61—H6130.9800
C2—N1—C6116.60 (9)H472—C47—H471109.5
N1—C2—N3126.73 (9)C46—C45—C44122.35 (10)
N1—C2—C21116.67 (9)C46—C45—H45118.8
N3—C2—C21116.55 (10)C44—C45—H45118.8
C22—C21—C26118.70 (10)C45—C46—C41119.72 (10)
C22—C21—C2120.54 (10)C45—C46—H46120.1
C26—C21—C2120.73 (10)C41—C46—H46120.1
C23—C22—C21120.65 (11)C6—C5—C4116.38 (9)
C23—C22—H22119.7C6—C5—C57123.37 (10)
C21—C22—H22119.7C4—C5—C57120.15 (9)
C24—C23—C22120.24 (11)N5—C57—C5111.50 (9)
C24—C23—H23119.9N5—C57—H571109.3
C22—C23—H23119.9C5—C57—H571109.3
C25—C24—C23119.80 (11)N5—C57—H572109.3
C25—C24—H24120.1C5—C57—H572109.3
C23—C24—H24120.1H571—C57—H572108.0
C24—C25—C26120.13 (11)C51—N5—C57116.18 (9)
C24—C25—H25119.9C51—N5—H5110.7 (7)
C26—C25—H25119.9C57—N5—H5109.2 (7)
C25—C26—C21120.47 (10)C56—C51—C52118.76 (10)
C25—C26—H26119.8C56—C51—N5120.78 (10)
C21—C26—H26119.8C52—C51—N5120.45 (10)
C4—N3—C2116.05 (9)C53—C52—C51120.76 (11)
N3—C4—N4119.36 (10)C53—C52—H52119.6
N3—C4—C5122.42 (9)C51—C52—H52119.6
N4—C4—C5118.22 (9)C54—C53—C52118.55 (11)
C4—N4—C41130.21 (9)C54—C53—H53120.7
C4—N4—H4114.2 (7)C52—C53—H53120.7
C41—N4—H4114.6 (7)C55—C54—F5118.87 (10)
C42—C41—C46118.41 (10)C55—C54—C53122.38 (10)
C42—C41—N4116.76 (10)F5—C54—C53118.75 (10)
C46—C41—N4124.71 (10)C54—C55—C56118.76 (11)
C43—C42—C41120.88 (10)C54—C55—H55120.6
C43—C42—H42119.6C56—C55—H55120.6
C41—C42—H42119.6C55—C56—C51120.78 (11)
C42—C43—C44121.60 (10)C55—C56—H56119.6
C42—C43—H43119.2C51—C56—H56119.6
C44—C43—H43119.2N1—C6—C5121.77 (10)
C43—C44—C45117.02 (10)N1—C6—C61114.84 (9)
C43—C44—C47121.06 (10)C5—C6—C61123.38 (9)
C45—C44—C47121.89 (10)C6—C61—H611109.5
C44—C47—H473109.5C6—C61—H612109.5
C44—C47—H472109.5H611—C61—H612109.5
H473—C47—H472109.5C6—C61—H613109.5
C44—C47—H471109.5H611—C61—H613109.5
H473—C47—H471109.5H612—C61—H613109.5
C6—N1—C2—N31.40 (15)C44—C45—C46—C41−0.85 (16)
C6—N1—C2—C21−175.79 (9)C42—C41—C46—C45−0.49 (14)
N1—C2—C21—C22−10.66 (14)N4—C41—C46—C45−176.22 (9)
N3—C2—C21—C22171.85 (9)N3—C4—C5—C6−1.67 (14)
N1—C2—C21—C26167.46 (9)N4—C4—C5—C6177.97 (9)
N3—C2—C21—C26−10.03 (14)N3—C4—C5—C57175.03 (9)
C26—C21—C22—C231.20 (16)N4—C4—C5—C57−5.32 (14)
C2—C21—C22—C23179.36 (10)C6—C5—C57—N5−116.78 (12)
C21—C22—C23—C24−0.62 (17)C4—C5—C57—N566.75 (13)
C22—C23—C24—C25−0.41 (17)C5—C57—N5—C51173.10 (9)
C23—C24—C25—C260.82 (17)C57—N5—C51—C56−132.72 (11)
C24—C25—C26—C21−0.22 (16)C57—N5—C51—C5248.62 (14)
C22—C21—C26—C25−0.78 (15)C56—C51—C52—C531.29 (15)
C2—C21—C26—C25−178.94 (10)N5—C51—C52—C53179.98 (10)
N1—C2—N3—C4−0.86 (15)C51—C52—C53—C54−0.79 (16)
C21—C2—N3—C4176.34 (9)C52—C53—C54—C55−0.40 (16)
C2—N3—C4—N4−178.66 (9)C52—C53—C54—F5178.85 (9)
C2—N3—C4—C50.98 (14)F5—C54—C55—C56−178.21 (9)
N3—C4—N4—C41−9.67 (16)C53—C54—C55—C561.04 (16)
C5—C4—N4—C41170.67 (10)C54—C55—C56—C51−0.50 (16)
C4—N4—C41—C42166.24 (10)C52—C51—C56—C55−0.64 (15)
C4—N4—C41—C46−17.97 (17)N5—C51—C56—C55−179.32 (10)
C46—C41—C42—C431.63 (14)C2—N1—C6—C5−2.09 (14)
N4—C41—C42—C43177.70 (9)C2—N1—C6—C61177.06 (9)
C41—C42—C43—C44−1.47 (15)C4—C5—C6—N12.23 (14)
C42—C43—C44—C450.12 (15)C57—C5—C6—N1−174.35 (9)
C42—C43—C44—C47−178.02 (10)C4—C5—C6—C61−176.85 (9)
C43—C44—C45—C461.03 (15)C57—C5—C6—C616.56 (15)
C47—C44—C45—C46179.16 (10)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the N1/C2/N3/C4–C6 ring.
D—H···AD—HH···AD···AD—H···A
N4—H4···N50.869 (11)2.294 (11)2.9820 (18)136.2 (9)
C57—H571···F5i0.992.543.440 (2)151
C57—H572···Cg1ii0.992.603.467 (7)147
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC25H23FN4
Mr398.47
Crystal system, space groupTriclinic, P1
Temperature (K)85
a, b, c (Å)8.306 (4), 10.070 (4), 12.234 (5)
α, β, γ (°)88.78 (4), 89.12 (4), 82.75 (5)
V (Å3)1014.8 (8)
Z2
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.36 × 0.18 × 0.14
Data collection
DiffractometerOxford Xcalibur PX
diffractometer with Onyx CCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		17245, 8461, 4334
Rint0.033
(sin θ/λ)max (Å−1)0.807
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.093, 1.00
No. of reflections8461
No. of parameters279
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.38, −0.31

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the N1/C2/N3/C4–C6 ring.
D—H···AD—HH···AD···AD—H···A
N4—H4···N50.869 (11)2.294 (11)2.9820 (18)136.2 (9)
C57—H571···F5i0.992.543.440 (2)151
C57—H572···Cg1ii0.992.603.467 (7)147
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x, −y+1, −z+1.
 

References

First citationCieplik, J., Pluta, J., Bryndal, I. & Lis, T. (2006). Acta Cryst. C62, o259–o261.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationCieplik, J., Pluta, J., Bryndal, I. & Lis, T. (2011). Acta Cryst. E67, o3162.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationCieplik, J., Pluta, J. & Gubrynowicz, O. (2003). Boll. Chim. Farm. 142, 146–150.  PubMed CAS Google Scholar
 First citationCieplik, J., Raginia, M., Pluta, J., Gubrynowicz, O., Bryndal, I. & Lis, T. (2008). Acta Pol. Pharm. Drug Res. 65, 427–434.  CAS Google Scholar
 First citationCieplik, J., Stolarczyk, M., Bryndal, I. & Lis, T. (2012). Acta Cryst. E68, o1729–o1730.  CSD CrossRef CAS IUCr Journals Google Scholar
 First citationCieplik, J., Stolarczyk, M., Pluta, J., Gubrynowicz, O., Bryndal, I., Lis, T. & Mikulewicz, M. (2011). Acta Pol. Pharm. Drug Res. 68, 57–65.  CAS Google Scholar
 First citationOxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS 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.

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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2922
https://doi.org/10.1107/S160053681203783X
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