5-[(4-Fluoro-anilino)meth-yl]-6-methyl-N-(4-methyl-phen-yl)-2-phenyl-pyrimidin-4-amine.

In the title compound, C(25)H(23)FN(4), 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 mol-ecular conformation is stabilized by an intra-molecular 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 mol-ecules into an inversion dimer with an R(2) (2)(16) motif. In the dimer, there is also an inter-molecular π-π stacking inter-action [centroid-centroid distance = 3.708 (4) Å] between the fluorinated benzene rings. The dimers are further linked by a C-H⋯π inter-action, 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 ▶, 2008 ▶); Cieplik, Stolarczyk et al. (2011 ▶). For related structures, see: Cieplik et al. (2006 ▶, 2012 ▶); Cieplik, Pluta et al. (2011 ▶).

Experimental

Crystal data

C25H23FN4

M = 398.47

Triclinic,

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)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 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

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681203783X/is5187sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203783X/is5187Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203783X/is5187Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H23FN4	Z = 2
Mr = 398.47	F(000) = 420
Triclinic, P1	Dx = 1.304 Mg m−3
Hall symbol: -P 1	Melting point: 424 K
a = 8.306 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.070 (4) Å	Cell parameters from 9708 reflections
c = 12.234 (5) Å	θ = 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) Å3	0.36 × 0.18 × 0.14 mm

Oxford Xcalibur PX diffractometer with Onyx CCD	4334 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 35.0°, θmin = 4.8°
φ and ω scans	h = −11→13
17245 measured reflections	k = −15→16
8461 independent reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H 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 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.10445 (10)	0.79035 (8)	0.41851 (7)	0.01576 (19)
C2	0.20919 (12)	0.71729 (10)	0.35266 (8)	0.0140 (2)
C21	0.25288 (12)	0.78216 (10)	0.24794 (8)	0.0146 (2)
C22	0.16726 (13)	0.90318 (10)	0.21321 (9)	0.0202 (2)
H22	0.0795	0.9441	0.2565	0.024*
C23	0.20876 (14)	0.96450 (11)	0.11618 (9)	0.0249 (3)
H23	0.1488	1.0466	0.0930	0.030*
C24	0.33733 (13)	0.90659 (11)	0.05289 (9)	0.0232 (3)
H24	0.3651	0.9485	−0.0139	0.028*
C25	0.42520 (13)	0.78748 (11)	0.08714 (9)	0.0223 (2)
H25	0.5144	0.7482	0.0443	0.027*
C26	0.38325 (13)	0.72516 (10)	0.18414 (8)	0.0185 (2)
H26	0.4438	0.6432	0.2071	0.022*
N3	0.28386 (10)	0.59329 (8)	0.37320 (7)	0.01478 (18)
C4	0.25062 (12)	0.53878 (10)	0.47043 (8)	0.0142 (2)
N4	0.32494 (10)	0.41352 (8)	0.49809 (7)	0.01661 (19)
H4	0.3281 (13)	0.3965 (11)	0.5680 (9)	0.020*
C41	0.42036 (12)	0.31806 (10)	0.43411 (8)	0.0152 (2)
C42	0.50900 (12)	0.21177 (10)	0.49004 (9)	0.0173 (2)
H42	0.5058	0.2087	0.5677	0.021*
C43	0.60151 (12)	0.11080 (10)	0.43404 (9)	0.0191 (2)
H43	0.6628	0.0406	0.4741	0.023*
C44	0.60703 (12)	0.10953 (10)	0.32041 (9)	0.0197 (2)
C47	0.70423 (14)	−0.00354 (12)	0.26030 (10)	0.0290 (3)
H473	0.7735	−0.0592	0.3120	0.043*
H472	0.7721	0.0333	0.2040	0.043*
H471	0.6303	−0.0582	0.2259	0.043*
C45	0.51525 (13)	0.21488 (10)	0.26533 (9)	0.0207 (2)
H45	0.5153	0.2158	0.1877	0.025*
C46	0.42383 (12)	0.31843 (10)	0.31983 (8)	0.0183 (2)
H46	0.3638	0.3893	0.2797	0.022*
C5	0.14131 (12)	0.60620 (10)	0.54702 (8)	0.0146 (2)
C57	0.09810 (12)	0.53600 (11)	0.65109 (8)	0.0181 (2)
H571	0.0099	0.5926	0.6897	0.022*
H572	0.0578	0.4507	0.6332	0.022*
N5	0.23857 (11)	0.50820 (9)	0.72329 (7)	0.0198 (2)
H5	0.2891 (13)	0.5843 (11)	0.7280 (9)	0.024*
C51	0.20720 (12)	0.45585 (10)	0.82908 (8)	0.0171 (2)
C52	0.11769 (13)	0.34826 (11)	0.84171 (9)	0.0210 (2)
H52	0.0775	0.3099	0.7790	0.025*
C53	0.08662 (13)	0.29654 (11)	0.94486 (9)	0.0215 (2)
H53	0.0245	0.2239	0.9535	0.026*
F5	0.11487 (8)	0.30347 (6)	1.13620 (5)	0.02904 (17)
C54	0.14766 (13)	0.35259 (10)	1.03413 (8)	0.0197 (2)
C55	0.23850 (13)	0.45671 (11)	1.02485 (9)	0.0228 (2)
H55	0.2808	0.4927	1.0880	0.027*
C56	0.26771 (13)	0.50879 (11)	0.92156 (9)	0.0215 (2)
H56	0.3298	0.5815	0.9140	0.026*
C6	0.07285 (12)	0.73425 (10)	0.51736 (8)	0.0154 (2)
C61	−0.03893 (13)	0.82245 (11)	0.59100 (9)	0.0211 (2)
H611	−0.1495	0.7992	0.5855	0.032*
H612	−0.0375	0.9164	0.5687	0.032*
H613	−0.0025	0.8093	0.6667	0.032*

	U11	U22	U33	U12	U13	U23
N1	0.0161 (4)	0.0172 (4)	0.0143 (4)	−0.0035 (3)	0.0008 (4)	0.0001 (4)
C2	0.0141 (5)	0.0158 (5)	0.0124 (5)	−0.0035 (4)	−0.0012 (4)	0.0000 (4)
C21	0.0174 (5)	0.0145 (5)	0.0125 (5)	−0.0040 (4)	−0.0001 (4)	−0.0001 (4)
C22	0.0250 (6)	0.0162 (5)	0.0187 (6)	0.0000 (4)	0.0028 (5)	0.0003 (4)
C23	0.0348 (7)	0.0175 (6)	0.0213 (6)	0.0001 (5)	0.0004 (5)	0.0055 (5)
C24	0.0314 (7)	0.0247 (6)	0.0150 (6)	−0.0107 (5)	0.0014 (5)	0.0041 (5)
C25	0.0221 (6)	0.0271 (6)	0.0177 (6)	−0.0042 (5)	0.0058 (5)	0.0010 (5)
C26	0.0199 (6)	0.0186 (5)	0.0162 (5)	−0.0006 (4)	0.0014 (4)	0.0017 (4)
N3	0.0156 (4)	0.0157 (4)	0.0135 (4)	−0.0038 (3)	0.0003 (3)	0.0012 (3)
C4	0.0147 (5)	0.0149 (5)	0.0138 (5)	−0.0042 (4)	−0.0007 (4)	−0.0001 (4)
N4	0.0215 (5)	0.0166 (5)	0.0109 (4)	0.0002 (4)	0.0017 (4)	0.0023 (4)
C41	0.0152 (5)	0.0138 (5)	0.0169 (5)	−0.0040 (4)	0.0016 (4)	0.0005 (4)
C42	0.0192 (5)	0.0178 (5)	0.0156 (5)	−0.0052 (4)	−0.0016 (4)	0.0012 (4)
C43	0.0176 (5)	0.0160 (5)	0.0236 (6)	−0.0022 (4)	−0.0036 (5)	0.0017 (4)
C44	0.0181 (5)	0.0182 (5)	0.0234 (6)	−0.0042 (4)	0.0015 (5)	−0.0026 (5)
C47	0.0305 (7)	0.0249 (6)	0.0308 (7)	0.0006 (5)	−0.0008 (5)	−0.0067 (5)
C45	0.0249 (6)	0.0218 (6)	0.0159 (6)	−0.0048 (5)	0.0018 (5)	−0.0018 (4)
C46	0.0210 (6)	0.0180 (5)	0.0156 (5)	−0.0016 (4)	−0.0014 (4)	0.0028 (4)
C5	0.0149 (5)	0.0180 (5)	0.0115 (5)	−0.0040 (4)	0.0002 (4)	0.0008 (4)
C57	0.0190 (6)	0.0212 (5)	0.0137 (5)	−0.0020 (4)	0.0031 (4)	0.0019 (4)
N5	0.0186 (5)	0.0262 (5)	0.0154 (5)	−0.0067 (4)	−0.0006 (4)	0.0043 (4)
C51	0.0148 (5)	0.0206 (5)	0.0148 (5)	0.0018 (4)	0.0020 (4)	0.0033 (4)
C52	0.0225 (6)	0.0257 (6)	0.0151 (6)	−0.0042 (5)	−0.0026 (5)	0.0000 (5)
C53	0.0222 (6)	0.0212 (6)	0.0210 (6)	−0.0032 (4)	0.0015 (5)	0.0044 (5)
F5	0.0398 (4)	0.0301 (4)	0.0151 (3)	0.0018 (3)	0.0043 (3)	0.0068 (3)
C54	0.0239 (6)	0.0205 (6)	0.0122 (5)	0.0055 (4)	0.0039 (4)	0.0053 (4)
C55	0.0299 (6)	0.0221 (6)	0.0155 (6)	0.0007 (5)	−0.0028 (5)	−0.0020 (5)
C56	0.0243 (6)	0.0195 (6)	0.0209 (6)	−0.0030 (4)	0.0002 (5)	0.0000 (5)
C6	0.0137 (5)	0.0188 (5)	0.0140 (5)	−0.0035 (4)	0.0001 (4)	−0.0011 (4)
C61	0.0224 (6)	0.0212 (6)	0.0190 (6)	−0.0009 (4)	0.0057 (5)	−0.0012 (4)

N1—C2	1.3377 (14)	C47—H473	0.9800
N1—C6	1.3598 (14)	C47—H472	0.9800
C2—N3	1.3427 (14)	C47—H471	0.9800
C2—C21	1.4865 (15)	C45—C46	1.3867 (16)
C21—C22	1.3928 (16)	C45—H45	0.9500
C21—C26	1.3955 (16)	C46—H46	0.9500
C22—C23	1.3853 (16)	C5—C6	1.3853 (15)
C22—H22	0.9500	C5—C57	1.5037 (15)
C23—C24	1.3845 (17)	C57—N5	1.4692 (15)
C23—H23	0.9500	C57—H571	0.9900
C24—C25	1.3835 (16)	C57—H572	0.9900
C24—H24	0.9500	N5—C51	1.4199 (14)
C25—C26	1.3908 (15)	N5—H5	0.922 (11)
C25—H25	0.9500	C51—C56	1.3884 (16)
C26—H26	0.9500	C51—C52	1.3940 (16)
N3—C4	1.3389 (13)	C52—C53	1.3879 (15)
C4—N4	1.3705 (14)	C52—H52	0.9500
C4—C5	1.4173 (15)	C53—C54	1.3726 (17)
N4—C41	1.4091 (15)	C53—H53	0.9500
N4—H4	0.869 (11)	F5—C54	1.3694 (13)
C41—C42	1.3932 (15)	C54—C55	1.3688 (16)
C41—C46	1.3980 (15)	C55—C56	1.3876 (16)
C42—C43	1.3820 (16)	C55—H55	0.9500
C42—H42	0.9500	C56—H56	0.9500
C43—C44	1.3905 (16)	C6—C61	1.5043 (16)
C43—H43	0.9500	C61—H611	0.9800
C44—C45	1.3935 (16)	C61—H612	0.9800
C44—C47	1.5081 (17)	C61—H613	0.9800
C2—N1—C6	116.60 (9)	H472—C47—H471	109.5
N1—C2—N3	126.73 (9)	C46—C45—C44	122.35 (10)
N1—C2—C21	116.67 (9)	C46—C45—H45	118.8
N3—C2—C21	116.55 (10)	C44—C45—H45	118.8
C22—C21—C26	118.70 (10)	C45—C46—C41	119.72 (10)
C22—C21—C2	120.54 (10)	C45—C46—H46	120.1
C26—C21—C2	120.73 (10)	C41—C46—H46	120.1
C23—C22—C21	120.65 (11)	C6—C5—C4	116.38 (9)
C23—C22—H22	119.7	C6—C5—C57	123.37 (10)
C21—C22—H22	119.7	C4—C5—C57	120.15 (9)
C24—C23—C22	120.24 (11)	N5—C57—C5	111.50 (9)
C24—C23—H23	119.9	N5—C57—H571	109.3
C22—C23—H23	119.9	C5—C57—H571	109.3
C25—C24—C23	119.80 (11)	N5—C57—H572	109.3
C25—C24—H24	120.1	C5—C57—H572	109.3
C23—C24—H24	120.1	H571—C57—H572	108.0
C24—C25—C26	120.13 (11)	C51—N5—C57	116.18 (9)
C24—C25—H25	119.9	C51—N5—H5	110.7 (7)
C26—C25—H25	119.9	C57—N5—H5	109.2 (7)
C25—C26—C21	120.47 (10)	C56—C51—C52	118.76 (10)
C25—C26—H26	119.8	C56—C51—N5	120.78 (10)
C21—C26—H26	119.8	C52—C51—N5	120.45 (10)
C4—N3—C2	116.05 (9)	C53—C52—C51	120.76 (11)
N3—C4—N4	119.36 (10)	C53—C52—H52	119.6
N3—C4—C5	122.42 (9)	C51—C52—H52	119.6
N4—C4—C5	118.22 (9)	C54—C53—C52	118.55 (11)
C4—N4—C41	130.21 (9)	C54—C53—H53	120.7
C4—N4—H4	114.2 (7)	C52—C53—H53	120.7
C41—N4—H4	114.6 (7)	C55—C54—F5	118.87 (10)
C42—C41—C46	118.41 (10)	C55—C54—C53	122.38 (10)
C42—C41—N4	116.76 (10)	F5—C54—C53	118.75 (10)
C46—C41—N4	124.71 (10)	C54—C55—C56	118.76 (11)
C43—C42—C41	120.88 (10)	C54—C55—H55	120.6
C43—C42—H42	119.6	C56—C55—H55	120.6
C41—C42—H42	119.6	C55—C56—C51	120.78 (11)
C42—C43—C44	121.60 (10)	C55—C56—H56	119.6
C42—C43—H43	119.2	C51—C56—H56	119.6
C44—C43—H43	119.2	N1—C6—C5	121.77 (10)
C43—C44—C45	117.02 (10)	N1—C6—C61	114.84 (9)
C43—C44—C47	121.06 (10)	C5—C6—C61	123.38 (9)
C45—C44—C47	121.89 (10)	C6—C61—H611	109.5
C44—C47—H473	109.5	C6—C61—H612	109.5
C44—C47—H472	109.5	H611—C61—H612	109.5
H473—C47—H472	109.5	C6—C61—H613	109.5
C44—C47—H471	109.5	H611—C61—H613	109.5
H473—C47—H471	109.5	H612—C61—H613	109.5
C6—N1—C2—N3	1.40 (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—C22	171.85 (9)	N3—C4—C5—C6	−1.67 (14)
N1—C2—C21—C26	167.46 (9)	N4—C4—C5—C6	177.97 (9)
N3—C2—C21—C26	−10.03 (14)	N3—C4—C5—C57	175.03 (9)
C26—C21—C22—C23	1.20 (16)	N4—C4—C5—C57	−5.32 (14)
C2—C21—C22—C23	179.36 (10)	C6—C5—C57—N5	−116.78 (12)
C21—C22—C23—C24	−0.62 (17)	C4—C5—C57—N5	66.75 (13)
C22—C23—C24—C25	−0.41 (17)	C5—C57—N5—C51	173.10 (9)
C23—C24—C25—C26	0.82 (17)	C57—N5—C51—C56	−132.72 (11)
C24—C25—C26—C21	−0.22 (16)	C57—N5—C51—C52	48.62 (14)
C22—C21—C26—C25	−0.78 (15)	C56—C51—C52—C53	1.29 (15)
C2—C21—C26—C25	−178.94 (10)	N5—C51—C52—C53	179.98 (10)
N1—C2—N3—C4	−0.86 (15)	C51—C52—C53—C54	−0.79 (16)
C21—C2—N3—C4	176.34 (9)	C52—C53—C54—C55	−0.40 (16)
C2—N3—C4—N4	−178.66 (9)	C52—C53—C54—F5	178.85 (9)
C2—N3—C4—C5	0.98 (14)	F5—C54—C55—C56	−178.21 (9)
N3—C4—N4—C41	−9.67 (16)	C53—C54—C55—C56	1.04 (16)
C5—C4—N4—C41	170.67 (10)	C54—C55—C56—C51	−0.50 (16)
C4—N4—C41—C42	166.24 (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—C43	1.63 (14)	C2—N1—C6—C5	−2.09 (14)
N4—C41—C42—C43	177.70 (9)	C2—N1—C6—C61	177.06 (9)
C41—C42—C43—C44	−1.47 (15)	C4—C5—C6—N1	2.23 (14)
C42—C43—C44—C45	0.12 (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—C46	1.03 (15)	C57—C5—C6—C61	6.56 (15)
C47—C44—C45—C46	179.16 (10)

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

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) ; (ii) .