4-(4-Fluoro-phen-yl)-6-(2-fur-yl)pyrimidin-2-amine.

Mol-ecules of the title compound, C(14)H(10)FN(3)O, are essentially planar and in the crystal structure they form dimers via hydrogen bonds, involving pyrimidinyl N atoms and amino H atoms, about inversion centers. The centroids of the furyl and pyrimidinyl rings are separated by 3.489 (2)Å, indicating π-π stacking inter-actions.

Related literature

For related literature, see: Colorado, & Brodbelt (1996 ▶); Bojarski et al. (1985 ▶); Fun et al. (2006 ▶); Gallagher et al. (2004 ▶); Hueso et al. (2003 ▶); Miranda et al. (2006 ▶); Varga et al. (2003 ▶).; Miyazaki et al. (2005 ▶).

Experimental

Crystal data

C14H10FN3O

M = 255.25

Monoclinic,

a = 11.629 (4) Å

b = 5.992 (3) Å

c = 16.389 (6) Å

β = 97.69 (2)°

V = 1131.7 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 (2) K

0.24 × 0.20 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.974, T max = 0.983

4617 measured reflections

2567 independent reflections

1935 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 1.03

2567 reflections

179 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.21 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012294/lh2621sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012294/lh2621Isup2.hkl

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

C14H10FN3O	F000 = 528
Mr = 255.25	Dx = 1.498 Mg m−3
Monoclinic, P21/c	Melting point = 513–515 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 11.629 (4) Å	Cell parameters from 4617 reflections
b = 5.992 (3) Å	θ = 3.6–27.5º
c = 16.389 (6) Å	µ = 0.11 mm−1
β = 97.69 (2)º	T = 173 (2) K
V = 1131.7 (8) Å3	Prism, colorless
Z = 4	0.24 × 0.20 × 0.16 mm

Nonius KappaCCD diffractometer	2567 independent reflections
Radiation source: fine-focus sealed tube	1935 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 173(2) K	θmax = 27.5º
ω and φ scans	θmin = 3.6º
Absorption correction: multi-scan(SORTAV; Blessing, 1997)	h = −14→15
Tmin = 0.974, Tmax = 0.983	k = −7→7
4617 measured reflections	l = −21→21

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.044	w = 1/[σ2(Fo2) + (0.061P)2 + 0.4P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.123	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.25 e Å−3
2567 reflections	Δρmin = −0.21 e Å−3
179 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (6)
Secondary atom site location: difference Fourier map

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
F1	1.25524 (8)	−0.3651 (2)	0.33665 (7)	0.0417 (3)
N1	0.78951 (10)	−0.1133 (2)	0.47173 (8)	0.0212 (3)
N2	0.63490 (10)	0.1576 (2)	0.46105 (8)	0.0214 (3)
N3	0.64102 (12)	−0.1403 (3)	0.55076 (8)	0.0260 (3)
H31	0.5641 (17)	−0.128 (3)	0.5524 (11)	0.031*
H32	0.6685 (16)	−0.273 (4)	0.5618 (11)	0.031*
O1	0.68164 (9)	0.57384 (19)	0.30924 (7)	0.0252 (3)
C1	0.94793 (12)	−0.0974 (3)	0.39086 (9)	0.0209 (3)
C2	0.98310 (14)	−0.3102 (3)	0.41767 (10)	0.0269 (4)
H2	0.9353	−0.3948	0.4488	0.032*
C3	1.08664 (14)	−0.4012 (3)	0.39983 (10)	0.0302 (4)
H3	1.1108	−0.5456	0.4191	0.036*
C4	1.15313 (13)	−0.2769 (3)	0.35368 (10)	0.0282 (4)
C5	1.12145 (14)	−0.0680 (3)	0.32395 (10)	0.0280 (4)
H5	1.1690	0.0130	0.2915	0.034*
C6	1.01768 (13)	0.0212 (3)	0.34272 (10)	0.0256 (4)
H6	0.9939	0.1649	0.3225	0.031*
C7	0.83900 (12)	−0.0007 (3)	0.41450 (9)	0.0203 (3)
C8	0.79028 (13)	0.1937 (3)	0.37932 (9)	0.0225 (3)
H8	0.8261	0.2737	0.3395	0.027*
C9	0.68719 (12)	0.2674 (3)	0.40437 (9)	0.0200 (3)
C10	0.68960 (12)	−0.0280 (3)	0.49192 (9)	0.0208 (3)
C11	0.62985 (12)	0.4679 (3)	0.36912 (9)	0.0207 (3)
C12	0.53195 (13)	0.5788 (3)	0.38160 (10)	0.0242 (4)
H12	0.4803	0.5406	0.4196	0.029*
C13	0.52194 (14)	0.7633 (3)	0.32661 (10)	0.0279 (4)
H13	0.4620	0.8722	0.3206	0.033*
C14	0.61369 (14)	0.7542 (3)	0.28479 (10)	0.0279 (4)
H14	0.6291	0.8584	0.2440	0.034*

	U11	U22	U33	U12	U13	U23
F1	0.0259 (5)	0.0527 (7)	0.0494 (6)	0.0132 (5)	0.0156 (4)	−0.0045 (5)
N1	0.0169 (6)	0.0245 (7)	0.0224 (6)	0.0016 (5)	0.0036 (5)	0.0019 (5)
N2	0.0184 (6)	0.0232 (7)	0.0229 (6)	0.0012 (5)	0.0041 (5)	−0.0007 (5)
N3	0.0201 (7)	0.0296 (8)	0.0296 (7)	0.0035 (6)	0.0085 (5)	0.0081 (6)
O1	0.0253 (6)	0.0242 (6)	0.0270 (6)	0.0029 (5)	0.0073 (5)	0.0040 (5)
C1	0.0165 (7)	0.0256 (8)	0.0208 (7)	0.0008 (6)	0.0031 (6)	−0.0022 (6)
C2	0.0242 (8)	0.0277 (9)	0.0300 (8)	0.0039 (7)	0.0078 (6)	0.0032 (7)
C3	0.0280 (8)	0.0300 (9)	0.0330 (9)	0.0095 (7)	0.0063 (7)	0.0016 (7)
C4	0.0185 (7)	0.0379 (10)	0.0285 (8)	0.0071 (7)	0.0048 (6)	−0.0080 (7)
C5	0.0233 (8)	0.0341 (10)	0.0283 (8)	−0.0024 (7)	0.0100 (6)	−0.0026 (7)
C6	0.0230 (7)	0.0270 (8)	0.0272 (8)	0.0025 (7)	0.0052 (6)	0.0006 (7)
C7	0.0178 (7)	0.0225 (8)	0.0205 (7)	−0.0013 (6)	0.0020 (6)	−0.0018 (6)
C8	0.0201 (7)	0.0245 (8)	0.0236 (7)	0.0005 (6)	0.0052 (6)	0.0023 (6)
C9	0.0185 (7)	0.0210 (8)	0.0203 (7)	−0.0004 (6)	0.0013 (6)	−0.0023 (6)
C10	0.0179 (7)	0.0238 (8)	0.0206 (7)	−0.0004 (6)	0.0030 (6)	−0.0012 (6)
C11	0.0198 (7)	0.0218 (8)	0.0207 (7)	−0.0007 (6)	0.0033 (6)	−0.0015 (6)
C12	0.0211 (7)	0.0243 (8)	0.0272 (8)	0.0010 (6)	0.0036 (6)	−0.0025 (7)
C13	0.0271 (8)	0.0228 (8)	0.0324 (9)	0.0047 (7)	−0.0008 (7)	−0.0002 (7)
C14	0.0328 (8)	0.0216 (8)	0.0283 (8)	0.0035 (7)	0.0004 (7)	0.0051 (7)

F1—C4	1.3623 (18)	C3—H3	0.9500
N1—C7	1.346 (2)	C4—C5	1.376 (3)
N1—C10	1.3503 (19)	C5—C6	1.391 (2)
N2—C10	1.346 (2)	C5—H5	0.9500
N2—C9	1.348 (2)	C6—H6	0.9500
N3—C10	1.359 (2)	C7—C8	1.387 (2)
N3—H31	0.902 (19)	C8—C9	1.390 (2)
N3—H32	0.87 (2)	C8—H8	0.9500
O1—C14	1.3667 (19)	C9—C11	1.456 (2)
O1—C11	1.3736 (18)	C11—C12	1.357 (2)
C1—C2	1.392 (2)	C12—C13	1.421 (2)
C1—C6	1.399 (2)	C12—H12	0.9500
C1—C7	1.491 (2)	C13—C14	1.344 (2)
C2—C3	1.388 (2)	C13—H13	0.9500
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.372 (2)
C7—N1—C10	116.33 (13)	N1—C7—C8	121.46 (14)
C10—N2—C9	115.37 (12)	N1—C7—C1	116.36 (14)
C10—N3—H31	119.2 (12)	C8—C7—C1	122.18 (14)
C10—N3—H32	115.2 (12)	C7—C8—C9	117.68 (14)
H31—N3—H32	114.2 (17)	C7—C8—H8	121.2
C14—O1—C11	106.44 (12)	C9—C8—H8	121.2
C2—C1—C6	118.38 (14)	N2—C9—C8	122.34 (14)
C2—C1—C7	119.86 (14)	N2—C9—C11	116.84 (13)
C6—C1—C7	121.76 (14)	C8—C9—C11	120.82 (14)
C3—C2—C1	121.33 (16)	N2—C10—N1	126.82 (14)
C3—C2—H2	119.3	N2—C10—N3	117.09 (13)
C1—C2—H2	119.3	N1—C10—N3	116.08 (14)
C4—C3—C2	118.14 (16)	C12—C11—O1	109.78 (14)
C4—C3—H3	120.9	C12—C11—C9	133.89 (15)
C2—C3—H3	120.9	O1—C11—C9	116.32 (13)
F1—C4—C3	118.27 (16)	C11—C12—C13	106.53 (15)
F1—C4—C5	118.67 (15)	C11—C12—H12	126.7
C3—C4—C5	123.06 (15)	C13—C12—H12	126.7
C4—C5—C6	118.06 (15)	C14—C13—C12	106.75 (14)
C4—C5—H5	121.0	C14—C13—H13	126.6
C6—C5—H5	121.0	C12—C13—H13	126.6
C5—C6—C1	121.00 (16)	C13—C14—O1	110.49 (14)
C5—C6—H6	119.5	C13—C14—H14	124.8
C1—C6—H6	119.5	O1—C14—H14	124.8
C6—C1—C2—C3	2.2 (2)	C10—N2—C9—C11	179.48 (13)
C7—C1—C2—C3	−177.11 (14)	C7—C8—C9—N2	0.3 (2)
C1—C2—C3—C4	−1.0 (2)	C7—C8—C9—C11	−178.93 (13)
C2—C3—C4—F1	179.47 (14)	C9—N2—C10—N1	−0.3 (2)
C2—C3—C4—C5	−0.5 (2)	C9—N2—C10—N3	178.41 (13)
F1—C4—C5—C6	−179.16 (14)	C7—N1—C10—N2	−0.3 (2)
C3—C4—C5—C6	0.8 (2)	C7—N1—C10—N3	−178.93 (13)
C4—C5—C6—C1	0.4 (2)	C14—O1—C11—C12	0.17 (17)
C2—C1—C6—C5	−1.8 (2)	C14—O1—C11—C9	179.54 (13)
C7—C1—C6—C5	177.43 (14)	N2—C9—C11—C12	1.5 (2)
C10—N1—C7—C8	0.8 (2)	C8—C9—C11—C12	−179.20 (16)
C10—N1—C7—C1	−178.73 (12)	N2—C9—C11—O1	−177.67 (13)
C2—C1—C7—N1	10.0 (2)	C8—C9—C11—O1	1.6 (2)
C6—C1—C7—N1	−169.28 (13)	O1—C11—C12—C13	0.07 (17)
C2—C1—C7—C8	−169.55 (14)	C9—C11—C12—C13	−179.15 (16)
C6—C1—C7—C8	11.2 (2)	C11—C12—C13—C14	−0.29 (18)
N1—C7—C8—C9	−0.9 (2)	C12—C13—C14—O1	0.40 (18)
C1—C7—C8—C9	178.66 (13)	C11—O1—C14—C13	−0.36 (17)
C10—N2—C9—C8	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···N2i	0.90 (2)	2.30 (2)	3.190 (2)	168 (2)
C5—H5···O1ii	0.95	2.58	3.474 (2)	157
C2—H2···N1	0.95	2.46	2.789 (2)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H31⋯N2i	0.90 (2)	2.30 (2)	3.190 (2)	168 (2)
C5—H5⋯O1ii	0.95	2.58	3.474 (2)	157
C2—H2⋯N1	0.95	2.46	2.789 (2)	100

Symmetry codes: (i) ; (ii) .