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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 67| Part 12| December 2011| Page o3162
https://doi.org/10.1107/S1600536811045028

N-(2-Fluoro­phen­yl)-5-[(4-meth­­oxy­phen­yl)amino­meth­yl]-6-methyl-2-phenyl­pyrimidin-4-amine

Jerzy Cieplik,a Janusz Pluta,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 14 October 2011; accepted 27 October 2011; online 5 November 2011)

The conformation of the title mol­ecule, C25H23FN4O, is mainly determined by an intra­molecular N—H⋯N hydrogen bond closing a six-membered ring and the dihedral angles between the pyrimidine ring and the three benzene rings which are 12.8 (2), 12.0 (2) and 86.1 (2)°. An intra­molecular N—H⋯F inter­action also occurs. The crystal stucture is stabilized by weak C—H⋯O and C—H⋯π inter­actions. An inter­molecular N—H⋯N inter­action is also observed.

Related literature

For anti­bacterial activity of 6-methyl-2-phenyl-5-substituted pyrimidine derivatives, see: Cieplik et al. (1995[Cieplik, J., Machoń, Z., Zimecki, M. & Wieczorek, Z. (1995). Il Farmaco, 50, 131-136.], 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.]); Pluta et al. (1996[Pluta, J., Flendrich, M. & Cieplik, J. (1996). Boll. Chim. Farm. 135, 459-464.]). For related structures, see: Cieplik et al. (2006[Cieplik, J., Pluta, J., Bryndal, I. & Lis, T. (2006). Acta Cryst. C62, o259-o261.]).

[Scheme 1]

Experimental

Crystal data

  • C25H23FN4O

  • Mr = 414.47

  • Monoclinic, C 2/c

  • a = 27.075 (11) Å

  • b = 8.922 (4) Å

  • c = 22.983 (10) Å

  • β = 132.22 (5)°

  • V = 4112 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 85 K

  • 0.53 × 0.17 × 0.14 mm
Data collection

  • Oxford Diffraction Xcalibur PX κ-geometry diffractometer

  • 28521 measured reflections

  • 10469 independent reflections

  • 7196 reflections with I > 2σ(I)

  • Rint = 0.025
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.121

  • S = 1.01

  • 10469 reflections

  • 288 parameters

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

  • Δρmax = 0.61 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1–C6, C41–C46 and C21–C26 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N4—H4⋯N5 0.88 (1) 2.07 (1) 2.794 (2) 139 (1)
N4—H4⋯F4 0.88 (1) 2.19 (1) 2.633 (1) 111 (1)
C61—H611⋯O5i 0.98 2.49 3.426 (2) 159
C61—H612⋯Cg1ii 0.98 2.69 3.381 (3) 128
C61—H613⋯Cg2iii 0.98 2.73 3.657 (3) 159
C53—H53⋯Cg3ii 0.95 2.74 3.634 (3) 156
N5—H5⋯N1iii 0.90 (1) 2.76 (1) 3.541 (2) 145 (1)
Symmetry codes: (i) [x, -y+1, z-{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -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 RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, 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: 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/S1600536811045028/gk2418sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045028/gk2418Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045028/gk2418Isup3.cml

checkCIF report


Comment top

Pyrimidines are very important molecules in biology and have many applications in the areas of pharmaceuticals. 6-Methyl-2-phenyl-4-thio-5-pyrimidine carboxylic acid is a key intermediate for our synthesis of a wide range of various 6-methyl-2-phenyl-5-substituted pyrimidine derivatives (Cieplik et al., 1995, 2003, 2008; Pluta et al., 1996). Microbiological testing of a number of such pyrimidine derivatives, designed and synthesized as immunomodulating agents, showed them to possess antibacterial and antifungal activity (Cieplik et al., 1995, 2003). In connection with these studies, we have described the structures of two polymorphic forms of N-(4-chlorophenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine (Cieplik et al., 2006). Now, we have prepared a new compound of this class of derivatives, namely N-(2-fluorophenyl)-5-[(4-methoxyphenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine and present its structure here. In the crystal, the orientation of the amine groups with respect to each other results from intramolecular N—H···N hydrogen bond between N4—H4 and N5, which closes six-membered ring. Conformation of the title molecule is best defined by the dihedral angles formed between the pyrimidine ring plane and the planes of the phenyl group attached to C2 and the benzene rings of the (2-fluorophenyl)amino or (4-methoxyphenyl)aminomethyl groups, attached to C4 or C5 of the pyrimidine ring. These dihedral angles are 12.8 (2)°, 12.0 (2)° and 86.1 (2)°, respectively. The twist of 12.8 (2)° of the phenyl group is similar to that found in the polymorphic forms of N-(4-chlorophenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine [5.2 (2)° and 6.4 (2)°; Cieplik et al., 2006]. Additionally, the aromatic atom C41 of the (2-fluorophenyl)amino group is nearly coplanar with the pyrimidine ring. The C51 atom of (4-methoxyphenyl)aminomethyl group deviates from the pyrimidine ring plane by -1.01 (1) Å.

Contrary to polymorhic forms of N-(4-chlorophenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine (Cieplik et al., 2006), the amine atom N5 does not participate in hydrogen bonding. The crystal structure of title compound is stabilized by weak C—H···O and C—H···π hydrogen bonds. In the crystal, the molecules are linked by C—H···O hydrogen bonds involving the methyl group C61 as a donor and O5 atom (x, -y + 1, z - 1/2) of the methoxy group as an acceptor. This interaction links the molecules into polymeric chains parallel to the c axis (Fig. 2). These chains are further linked by C—H···π interactions. The methyl group C61 acts as a donor to the fluorinated aryl ring C41—C46 (symmetry code: -x + 1/2, -y + 3/2, -z + 1) and also to the pirymidine ring (-x + 1/2, -y + 1/2, -z + 1). Additionally, the C53—H53 group acts as a donor of C—H···π(arene) interaction to the benzene ring C21—C26 (-x + 1/2, -y + 3/2, -z + 1). Combination of these interactions leads to layers of molecules parallel to the bc plane (Fig. 3).

Related literature top

For antibacterial activity of 6-methyl-2-phenyl-5-substituted pyrimidine derivatives, see: Cieplik et al. (1995, 2003, 2008); Pluta et al. (1996). For related structures, see: Cieplik et al. (2006).

Experimental top

The title compound was obtained by adopting the procedure described previously by Cieplik et al. (2003). 4 g (0.0122 mmol) of 5-(chloromethyl)-N-(2-fluorophenyl)-6-methyl-2-phenylpyrimidin-4-amine was dissolved in 50 ml of chloroform, and 2 g of 4-methoxyaniline was added. The reaction mixture was refluxed for 6 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: 78.5%, m.p. 157–158 °C).

Refinement top

The N-bonded H atoms were found from difference Fourier maps and 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 refined with Uiso(H)=1.2Ueq(C) except methyl groups where Uiso(H)=1.5 Ueq(C).

Structure description top

Pyrimidines are very important molecules in biology and have many applications in the areas of pharmaceuticals. 6-Methyl-2-phenyl-4-thio-5-pyrimidine carboxylic acid is a key intermediate for our synthesis of a wide range of various 6-methyl-2-phenyl-5-substituted pyrimidine derivatives (Cieplik et al., 1995, 2003, 2008; Pluta et al., 1996). Microbiological testing of a number of such pyrimidine derivatives, designed and synthesized as immunomodulating agents, showed them to possess antibacterial and antifungal activity (Cieplik et al., 1995, 2003). In connection with these studies, we have described the structures of two polymorphic forms of N-(4-chlorophenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine (Cieplik et al., 2006). Now, we have prepared a new compound of this class of derivatives, namely N-(2-fluorophenyl)-5-[(4-methoxyphenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine and present its structure here. In the crystal, the orientation of the amine groups with respect to each other results from intramolecular N—H···N hydrogen bond between N4—H4 and N5, which closes six-membered ring. Conformation of the title molecule is best defined by the dihedral angles formed between the pyrimidine ring plane and the planes of the phenyl group attached to C2 and the benzene rings of the (2-fluorophenyl)amino or (4-methoxyphenyl)aminomethyl groups, attached to C4 or C5 of the pyrimidine ring. These dihedral angles are 12.8 (2)°, 12.0 (2)° and 86.1 (2)°, respectively. The twist of 12.8 (2)° of the phenyl group is similar to that found in the polymorphic forms of N-(4-chlorophenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine [5.2 (2)° and 6.4 (2)°; Cieplik et al., 2006]. Additionally, the aromatic atom C41 of the (2-fluorophenyl)amino group is nearly coplanar with the pyrimidine ring. The C51 atom of (4-methoxyphenyl)aminomethyl group deviates from the pyrimidine ring plane by -1.01 (1) Å.

Contrary to polymorhic forms of N-(4-chlorophenyl)-5-[(4-chlorophenyl)aminomethyl]-6-methyl-2-phenylpyrimidin-4-amine (Cieplik et al., 2006), the amine atom N5 does not participate in hydrogen bonding. The crystal structure of title compound is stabilized by weak C—H···O and C—H···π hydrogen bonds. In the crystal, the molecules are linked by C—H···O hydrogen bonds involving the methyl group C61 as a donor and O5 atom (x, -y + 1, z - 1/2) of the methoxy group as an acceptor. This interaction links the molecules into polymeric chains parallel to the c axis (Fig. 2). These chains are further linked by C—H···π interactions. The methyl group C61 acts as a donor to the fluorinated aryl ring C41—C46 (symmetry code: -x + 1/2, -y + 3/2, -z + 1) and also to the pirymidine ring (-x + 1/2, -y + 1/2, -z + 1). Additionally, the C53—H53 group acts as a donor of C—H···π(arene) interaction to the benzene ring C21—C26 (-x + 1/2, -y + 3/2, -z + 1). Combination of these interactions leads to layers of molecules parallel to the bc plane (Fig. 3).

For antibacterial activity of 6-methyl-2-phenyl-5-substituted pyrimidine derivatives, see: Cieplik et al. (1995, 2003, 2008); Pluta et al. (1996). For related structures, see: Cieplik et al. (2006).

Computing details top

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

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level and H atoms shown as small spheres of arbitrary radii. The dotted line indicates an intramolecular N—H···N hydrogen bond.
[Figure 2] Fig. 2. Part of the crystal structure viewed down the b axis showing the chain formed via C—H···O hydrogen bonds. Dotted and dashed lines indicate intra- and intermolecular hydrogen bonds, respectively. H atoms not involved in hydrogen bonding have been omitted for clarity.
[Figure 3] Fig. 3. A packing diagram of title compound, showing C—H···π interactions. Intermolecular C—H···O interactions are shown with dashed lines, C—H···π interactions with double dashed lines and intramolecular N—H···N interactions with dotted lines. H atoms not involved in hydrogen bonding have been omitted for clarity.
N-(2-Fluorophenyl)-5-[(4-methoxyphenyl)aminomethyl]-6-methyl-2- phenylpyrimidin-4-amine top
Crystal data top
C25H23FN4OF(000) = 1744
Mr = 414.47Dx = 1.339 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 14660 reflections
a = 27.075 (11) Åθ = 4.2–38.5°
b = 8.922 (4) ŵ = 0.09 mm−1
c = 22.983 (10) ÅT = 85 K
β = 132.22 (5)°Block, light yellow
V = 4112 (3) Å30.53 × 0.17 × 0.14 mm
Z = 8
Data collection top
Oxford Diffraction Xcalibur PX κ-geometry
diffractometer		7196 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 38.5°, θmin = 4.2°
φ and ω scansh = −46→40
28521 measured reflectionsk = −12→15
10469 independent reflectionsl = −35→39
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.070P)2]
where P = (Fo2 + 2Fc2)/3
10469 reflections(Δ/σ)max = 0.001
288 parametersΔρmax = 0.61 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C25H23FN4OV = 4112 (3) Å3
Mr = 414.47Z = 8
Monoclinic, C2/cMo Kα radiation
a = 27.075 (11) ŵ = 0.09 mm−1
b = 8.922 (4) ÅT = 85 K
c = 22.983 (10) Å0.53 × 0.17 × 0.14 mm
β = 132.22 (5)°
Data collection top
Oxford Diffraction Xcalibur PX κ-geometry
diffractometer		7196 reflections with I > 2σ(I)
28521 measured reflectionsRint = 0.025
10469 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.61 e Å−3
10469 reflectionsΔρmin = −0.22 e Å−3
288 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
N10.23426 (3)0.36669 (7)0.40998 (3)0.01317 (11)
C20.17473 (4)0.43335 (8)0.36504 (4)0.01210 (12)
C210.12462 (4)0.39073 (8)0.28059 (4)0.01287 (12)
C220.14297 (4)0.30769 (8)0.24607 (4)0.01447 (13)
H220.18840.28090.27630.017*
C230.09517 (4)0.26420 (9)0.16781 (4)0.01767 (14)
H230.10810.20750.14490.021*
C240.02852 (4)0.30321 (9)0.12281 (5)0.02034 (16)
H24−0.00410.27210.06950.024*
C250.00996 (4)0.38787 (10)0.15623 (5)0.02228 (16)
H25−0.03540.41570.12560.027*
C260.05782 (4)0.43180 (10)0.23455 (4)0.01855 (14)
H260.04490.49040.25700.022*
N30.15437 (3)0.53341 (7)0.38901 (3)0.01317 (11)
C40.19708 (4)0.56283 (8)0.46609 (4)0.01252 (12)
N40.17917 (3)0.66198 (7)0.49490 (4)0.01472 (12)
H40.2030 (5)0.6531 (12)0.5456 (6)0.018*
C410.11961 (4)0.74116 (8)0.45602 (4)0.01369 (12)
C420.11209 (4)0.81165 (8)0.50421 (4)0.01637 (14)
F40.16300 (3)0.79604 (6)0.58317 (3)0.02284 (11)
C430.05679 (4)0.89387 (9)0.47602 (5)0.02065 (15)
H430.05390.93900.51110.025*
C440.00524 (4)0.90943 (10)0.39507 (5)0.02180 (16)
H44−0.03380.96420.37400.026*
C450.01153 (4)0.84392 (10)0.34542 (5)0.02132 (16)
H45−0.02330.85630.29020.026*
C460.06771 (4)0.76038 (9)0.37476 (4)0.01719 (14)
H460.07080.71650.33960.021*
C50.26157 (4)0.49669 (8)0.52009 (4)0.01261 (12)
C570.30861 (4)0.53792 (9)0.60615 (4)0.01576 (13)
H5710.34920.47500.63580.019*
H5720.32230.64400.61270.019*
N50.27693 (3)0.51636 (7)0.63795 (4)0.01484 (12)
H50.2652 (5)0.4199 (13)0.6350 (6)0.018*
C510.30334 (4)0.58811 (8)0.70885 (4)0.01285 (12)
C520.33894 (4)0.72198 (8)0.73410 (4)0.01505 (13)
H520.34950.76340.70550.018*
C530.35944 (4)0.79668 (8)0.80092 (4)0.01564 (13)
H530.38340.88820.81710.019*
C540.34466 (4)0.73683 (8)0.84340 (4)0.01471 (13)
O50.36179 (3)0.80239 (6)0.90928 (3)0.02145 (13)
C580.39084 (5)0.94760 (9)0.92941 (5)0.02204 (16)
H5810.43320.94220.94170.033*
H5820.39900.98480.97530.033*
H5830.36041.01590.88500.033*
C550.30912 (4)0.60230 (8)0.81897 (4)0.01540 (13)
H550.29880.56100.84780.018*
C560.28893 (4)0.52895 (8)0.75279 (4)0.01431 (13)
H560.26500.43740.73690.017*
C60.27830 (4)0.40137 (8)0.48783 (4)0.01261 (12)
C610.34603 (4)0.33005 (9)0.53604 (4)0.01562 (13)
H6110.34740.26750.50210.023*
H6120.35470.26780.57720.023*
H6130.38010.40840.56020.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0143 (3)0.0145 (3)0.0130 (2)0.0007 (2)0.0101 (2)0.00032 (19)
C20.0143 (3)0.0121 (3)0.0127 (3)0.0001 (2)0.0103 (2)0.0006 (2)
C210.0147 (3)0.0129 (3)0.0128 (3)−0.0003 (2)0.0100 (2)0.0001 (2)
C220.0167 (3)0.0139 (3)0.0142 (3)0.0011 (2)0.0110 (3)−0.0002 (2)
C230.0225 (4)0.0154 (3)0.0152 (3)0.0009 (3)0.0127 (3)−0.0015 (2)
C240.0219 (4)0.0185 (3)0.0149 (3)−0.0009 (3)0.0101 (3)−0.0025 (3)
C250.0154 (3)0.0271 (4)0.0175 (3)0.0011 (3)0.0082 (3)−0.0034 (3)
C260.0158 (3)0.0227 (4)0.0172 (3)0.0004 (3)0.0111 (3)−0.0031 (3)
N30.0159 (3)0.0133 (3)0.0130 (2)0.0015 (2)0.0108 (2)0.00088 (19)
C40.0158 (3)0.0115 (3)0.0136 (3)0.0006 (2)0.0112 (2)0.0008 (2)
N40.0171 (3)0.0160 (3)0.0125 (2)0.0041 (2)0.0105 (2)0.0012 (2)
C410.0165 (3)0.0115 (3)0.0168 (3)0.0010 (2)0.0127 (3)0.0006 (2)
C420.0215 (3)0.0143 (3)0.0186 (3)0.0011 (3)0.0156 (3)0.0005 (2)
F40.0304 (3)0.0232 (3)0.0176 (2)0.0073 (2)0.0172 (2)0.00160 (18)
C430.0261 (4)0.0173 (3)0.0278 (4)0.0026 (3)0.0219 (3)−0.0006 (3)
C440.0181 (3)0.0187 (4)0.0292 (4)0.0020 (3)0.0162 (3)−0.0018 (3)
C450.0167 (3)0.0206 (4)0.0214 (3)0.0021 (3)0.0106 (3)−0.0014 (3)
C460.0166 (3)0.0177 (3)0.0170 (3)0.0017 (3)0.0112 (3)−0.0008 (2)
C50.0141 (3)0.0130 (3)0.0123 (3)−0.0001 (2)0.0094 (2)0.0003 (2)
C570.0149 (3)0.0204 (3)0.0134 (3)−0.0007 (3)0.0100 (3)−0.0023 (2)
N50.0194 (3)0.0149 (3)0.0129 (2)−0.0030 (2)0.0120 (2)−0.0010 (2)
C510.0133 (3)0.0143 (3)0.0114 (3)0.0012 (2)0.0085 (2)0.0012 (2)
C520.0196 (3)0.0153 (3)0.0144 (3)−0.0015 (3)0.0131 (3)0.0006 (2)
C530.0201 (3)0.0143 (3)0.0156 (3)−0.0019 (3)0.0132 (3)−0.0004 (2)
C540.0194 (3)0.0143 (3)0.0143 (3)0.0017 (2)0.0129 (3)0.0012 (2)
O50.0370 (3)0.0165 (3)0.0200 (3)−0.0041 (2)0.0229 (3)−0.0029 (2)
C580.0306 (4)0.0176 (4)0.0187 (3)−0.0027 (3)0.0169 (3)−0.0031 (3)
C550.0204 (3)0.0145 (3)0.0173 (3)0.0018 (3)0.0151 (3)0.0025 (2)
C560.0165 (3)0.0138 (3)0.0163 (3)−0.0007 (2)0.0125 (3)0.0009 (2)
C60.0142 (3)0.0128 (3)0.0134 (3)0.0001 (2)0.0103 (2)0.0010 (2)
C610.0153 (3)0.0176 (3)0.0154 (3)0.0025 (3)0.0109 (3)0.0014 (2)
Geometric parameters (Å, º) top
N1—C21.3345 (13)C45—H450.9500
N1—C61.3607 (15)C46—H460.9500
C2—N31.3461 (10)C5—C61.3890 (11)
C2—C211.4878 (16)C5—C571.5112 (16)
C21—C261.3974 (15)C57—N51.4661 (11)
C21—C221.3984 (11)C57—H5710.9900
C22—C231.3899 (16)C57—H5720.9900
C22—H220.9500N5—C511.4178 (12)
C23—C241.3925 (16)N5—H50.904 (11)
C23—H230.9500C51—C521.3931 (12)
C24—C251.3900 (13)C51—C561.4073 (11)
C24—H240.9500C52—C531.4019 (12)
C25—C261.3921 (16)C52—H520.9500
C25—H250.9500C53—C541.3868 (11)
C26—H260.9500C53—H530.9500
N3—C41.3384 (14)C54—O51.3807 (11)
C4—N41.3739 (10)C54—C551.3985 (12)
C4—C51.4230 (15)O5—C581.4220 (12)
N4—C411.4004 (13)C58—H5810.9800
N4—H40.879 (11)C58—H5820.9800
C41—C461.4018 (17)C58—H5830.9800
C41—C421.4024 (11)C55—C561.3867 (12)
C42—F41.3605 (16)C55—H550.9500
C42—C431.3770 (13)C56—H560.9500
C43—C441.3924 (18)C6—C611.5050 (15)
C43—H430.9500C61—H6110.9800
C44—C451.3905 (13)C61—H6120.9800
C44—H440.9500C61—H6130.9800
C45—C461.3948 (13)
C2—N1—C6116.86 (8)C6—C5—C4115.94 (8)
N1—C2—N3126.33 (7)C6—C5—C57123.87 (7)
N1—C2—C21117.65 (8)C4—C5—C57120.10 (8)
N3—C2—C21115.98 (7)N5—C57—C5111.08 (8)
C26—C21—C22118.80 (8)N5—C57—H571109.4
C26—C21—C2120.16 (9)C5—C57—H571109.4
C22—C21—C2121.03 (8)N5—C57—H572109.4
C23—C22—C21120.35 (8)C5—C57—H572109.4
C23—C22—H22119.8H571—C57—H572108.0
C21—C22—H22119.8C51—N5—C57120.10 (7)
C22—C23—C24120.43 (9)C51—N5—H5113.4 (6)
C22—C23—H23119.8C57—N5—H5112.4 (7)
C24—C23—H23119.8C52—C51—C56118.06 (7)
C25—C24—C23119.65 (8)C52—C51—N5122.64 (7)
C25—C24—H24120.2C56—C51—N5119.11 (7)
C23—C24—H24120.2C51—C52—C53121.18 (7)
C24—C25—C26119.96 (8)C51—C52—H52119.4
C24—C25—H25120.0C53—C52—H52119.4
C26—C25—H25120.0C54—C53—C52119.94 (8)
C25—C26—C21120.79 (9)C54—C53—H53120.0
C25—C26—H26119.6C52—C53—H53120.0
C21—C26—H26119.6O5—C54—C53124.45 (7)
C4—N3—C2116.40 (7)O5—C54—C55115.93 (7)
N3—C4—N4119.57 (7)C53—C54—C55119.61 (7)
N3—C4—C5122.37 (8)C54—O5—C58116.58 (6)
N4—C4—C5118.05 (7)O5—C58—H581109.5
C4—N4—C41130.19 (7)O5—C58—H582109.5
C4—N4—H4113.6 (7)H581—C58—H582109.5
C41—N4—H4113.3 (7)O5—C58—H583109.5
N4—C41—C46127.26 (8)H581—C58—H583109.5
N4—C41—C42116.00 (8)H582—C58—H583109.5
C46—C41—C42116.73 (8)C56—C55—C54120.20 (7)
F4—C42—C43119.27 (8)C56—C55—H55119.9
F4—C42—C41116.93 (8)C54—C55—H55119.9
C43—C42—C41123.80 (9)C55—C56—C51121.01 (8)
C42—C43—C44118.59 (9)C55—C56—H56119.5
C42—C43—H43120.7C51—C56—H56119.5
C44—C43—H43120.7N1—C6—C5121.95 (7)
C45—C44—C43119.27 (8)N1—C6—C61115.44 (8)
C45—C44—H44120.4C5—C6—C61122.62 (8)
C43—C44—H44120.4C6—C61—H611109.5
C44—C45—C46121.54 (9)C6—C61—H612109.5
C44—C45—H45119.2H611—C61—H612109.5
C46—C45—H45119.2C6—C61—H613109.5
C45—C46—C41120.04 (8)H611—C61—H613109.5
C45—C46—H46120.0H612—C61—H613109.5
C41—C46—H46120.0
C6—N1—C2—N31.13 (11)C44—C45—C46—C41−0.17 (13)
C6—N1—C2—C21−176.79 (6)N4—C41—C46—C45−179.60 (8)
N1—C2—C21—C26166.64 (7)C42—C41—C46—C45−1.20 (11)
N3—C2—C21—C26−11.50 (10)N3—C4—C5—C61.19 (10)
N1—C2—C21—C22−12.51 (10)N4—C4—C5—C6−177.79 (6)
N3—C2—C21—C22169.35 (7)N3—C4—C5—C57177.97 (7)
C26—C21—C22—C23−1.44 (11)N4—C4—C5—C57−1.00 (10)
C2—C21—C22—C23177.72 (7)C6—C5—C57—N5−129.73 (8)
C21—C22—C23—C240.23 (12)C4—C5—C57—N553.76 (10)
C22—C23—C24—C250.84 (12)C5—C57—N5—C51−161.21 (6)
C23—C24—C25—C26−0.68 (13)C57—N5—C51—C5227.18 (11)
C24—C25—C26—C21−0.55 (13)C57—N5—C51—C56−157.88 (7)
C22—C21—C26—C251.60 (12)C56—C51—C52—C53−0.53 (11)
C2—C21—C26—C25−177.57 (7)N5—C51—C52—C53174.46 (7)
N1—C2—N3—C4−3.45 (11)C51—C52—C53—C540.40 (12)
C21—C2—N3—C4174.50 (6)C52—C53—C54—O5−179.13 (7)
C2—N3—C4—N4−178.93 (6)C52—C53—C54—C55−0.22 (12)
C2—N3—C4—C52.12 (10)C53—C54—O5—C586.20 (11)
N3—C4—N4—C411.78 (12)C55—C54—O5—C58−172.75 (7)
C5—C4—N4—C41−179.22 (7)O5—C54—C55—C56179.18 (7)
C4—N4—C41—C46−13.42 (13)C53—C54—C55—C560.17 (12)
C4—N4—C41—C42168.17 (7)C54—C55—C56—C51−0.31 (11)
N4—C41—C42—F4−0.01 (10)C52—C51—C56—C550.48 (11)
C46—C41—C42—F4−178.59 (7)N5—C51—C56—C55−174.69 (7)
N4—C41—C42—C43−179.89 (8)C2—N1—C6—C52.61 (10)
C46—C41—C42—C431.53 (12)C2—N1—C6—C61−177.14 (6)
F4—C42—C43—C44179.69 (7)C4—C5—C6—N1−3.64 (10)
C41—C42—C43—C44−0.43 (13)C57—C5—C6—N1179.71 (7)
C42—C43—C44—C45−1.00 (13)C4—C5—C6—C61176.09 (7)
C43—C44—C45—C461.31 (13)C57—C5—C6—C61−0.56 (11)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the N1–C6, C41–C46 and C21–C26 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N4—H4···N50.88 (1)2.07 (1)2.794 (2)139 (1)
N4—H4···F40.88 (1)2.19 (1)2.633 (1)111 (1)
C61—H611···O5i0.982.493.426 (2)159
C61—H612···Cg1ii0.982.693.381 (3)128
C61—H613···Cg2iii0.982.733.657 (3)159
C53—H53···Cg3ii0.952.743.634 (3)156
N5—H5···N1iii0.90 (1)2.76 (1)3.541 (2)145 (1)
Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x+1/2, −y+3/2, −z+1; (iii) −x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formulaC25H23FN4O
Mr414.47
Crystal system, space groupMonoclinic, C2/c
Temperature (K)85
a, b, c (Å)27.075 (11), 8.922 (4), 22.983 (10)
β (°) 132.22 (5)
V (Å3)4112 (3)
Z8
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.53 × 0.17 × 0.14
Data collection
DiffractometerOxford Diffraction Xcalibur PX κ-geometry
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		28521, 10469, 7196
Rint0.025
(sin θ/λ)max (Å−1)0.876
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.121, 1.01
No. of reflections10469
No. of parameters288
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.61, −0.22

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, Cg2 and Cg3 are the centroids of the N1–C6, C41–C46 and C21–C26 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N4—H4···N50.88 (1)2.07 (1)2.794 (2)139 (1)
N4—H4···F40.88 (1)2.19 (1)2.633 (1)111 (1)
C61—H611···O5i0.982.493.426 (2)159
C61—H612···Cg1ii0.982.693.381 (3)128
C61—H613···Cg2iii0.982.733.657 (3)159
C53—H53···Cg3ii0.952.743.634 (3)156
N5—H5···N1iii0.90 (1)2.76 (1)3.541 (2)145 (1)
Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x+1/2, −y+3/2, −z+1; (iii) −x+1/2, −y+1/2, −z+1.
 

References

First citationCieplik, J., Machoń, Z., Zimecki, M. & Wieczorek, Z. (1995). Il Farmaco, 50, 131–136.  CAS Google Scholar
 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. & 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 citationOxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.  Google Scholar
 First citationPluta, J., Flendrich, M. & Cieplik, J. (1996). Boll. Chim. Farm. 135, 459–464.  CAS PubMed Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3162
https://doi.org/10.1107/S1600536811045028
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