6-(2,6-Dimethyl-phen-yl)pyrido[2,3-d]pyrimidin-7-amine.

In the title compound, C(15)H(14)N(4), the pyrido[2,3-d]pyrimidine system is almost ideally planar (r.m.s. deviation 0.028 Å) with its mean plane almost orthogonal to the 2,6-dimethyl-phenyl plane. The dihedral angle formed by these planes [87.3 (2)°] is close to the predicted value (89.7°) obtained by mol-ecular-mechanics force-field calculations. Only one of the two active amine H atoms participates in hydrogen bonding, which links mol-ecules into centrosymmetric dimers.

Related literature

For the structures of related pyrido[2,3-d]pyrimidine derivatives, see: Hamby et al. (1997 ▶); Trumpp-Kallmeyer et al. (1998 ▶). For the synthesis of the title compound, see: Bennett et al. (1981 ▶); Blankley & Bennett (1981 ▶). For mol­ecular-mechanics force-field calculations, see: Duan et al. (2003 ▶).

Experimental

Crystal data

C15H14N4

M = 250.30

Monoclinic,

a = 16.272 (3) Å

b = 10.644 (2) Å

c = 15.234 (3) Å

β = 109.118 (3)°

V = 2493.0 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 208 K

0.14 × 0.06 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.988, T max = 0.995

6161 measured reflections

2863 independent reflections

1706 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.152

S = 0.98

2863 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-32 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006242/rz2295sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006242/rz2295Isup2.hkl

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

C15H14N4	F(000) = 1056
Mr = 250.30	Dx = 1.334 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1859 reflections
a = 16.272 (3) Å	θ = 2.3–27.8°
b = 10.644 (2) Å	µ = 0.08 mm−1
c = 15.234 (3) Å	T = 208 K
β = 109.118 (3)°	Block, colorless
V = 2493.0 (8) Å3	0.14 × 0.06 × 0.06 mm
Z = 8

Bruker Kappa-APEX2 CCD area-detector diffractometer	2863 independent reflections
Radiation source: fine-focus sealed tube	1706 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 28.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −21→21
Tmin = 0.988, Tmax = 0.995	k = −13→10
6161 measured reflections	l = −11→20

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0773P)2] where P = (Fo2 + 2Fc2)/3
2863 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 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
C1	0.60306 (12)	0.28432 (17)	0.63650 (12)	0.0292 (4)
C2	0.66357 (12)	0.27235 (16)	0.58459 (13)	0.0286 (4)
C3	0.56152 (12)	0.17232 (17)	0.46410 (13)	0.0298 (4)
C4	0.46019 (14)	0.0833 (2)	0.34015 (15)	0.0425 (5)
H4	0.4461	0.0508	0.2796	0.051*
C5	0.41654 (13)	0.12949 (19)	0.46163 (14)	0.0386 (5)
H5	0.3743	0.1300	0.4914	0.046*
C6	0.49866 (12)	0.17682 (17)	0.50973 (13)	0.0309 (4)
C7	0.52301 (12)	0.23505 (18)	0.59840 (13)	0.0323 (5)
H7	0.4829	0.2392	0.6308	0.039*
C8	0.62801 (12)	0.35600 (18)	0.72563 (13)	0.0302 (4)
C9	0.66754 (12)	0.29645 (19)	0.81040 (13)	0.0322 (5)
C10	0.68565 (13)	0.3677 (2)	0.89141 (14)	0.0389 (5)
H10	0.7113	0.3285	0.9493	0.047*
C11	0.66687 (14)	0.4936 (2)	0.88847 (15)	0.0456 (6)
H11	0.6798	0.5399	0.9439	0.055*
C12	0.62906 (14)	0.5519 (2)	0.80438 (15)	0.0451 (6)
H12	0.6164	0.6382	0.8028	0.054*
C13	0.60939 (12)	0.48549 (19)	0.72209 (13)	0.0355 (5)
C14	0.69087 (15)	0.1587 (2)	0.81607 (15)	0.0472 (6)
H14A	0.6435	0.1098	0.8241	0.071*
H14B	0.7433	0.1446	0.8685	0.071*
H14C	0.7008	0.1331	0.7592	0.071*
C15	0.56830 (15)	0.5511 (2)	0.63050 (15)	0.0500 (6)
H15A	0.5664	0.6408	0.6409	0.075*
H15B	0.5097	0.5197	0.6016	0.075*
H15C	0.6024	0.5350	0.5901	0.075*
N1	0.64297 (10)	0.21747 (15)	0.50164 (10)	0.0315 (4)
N2	0.54103 (11)	0.12193 (16)	0.37767 (11)	0.0377 (4)
N3	0.39463 (11)	0.08379 (17)	0.37626 (12)	0.0435 (5)
N4	0.74304 (10)	0.32180 (15)	0.61956 (11)	0.0375 (4)
H4A	0.7791	0.3174	0.5883	0.045*
H4B	0.7587	0.3584	0.6736	0.045*

	U11	U22	U33	U12	U13	U23
C1	0.0304 (10)	0.0319 (10)	0.0273 (10)	0.0037 (8)	0.0122 (8)	0.0018 (8)
C2	0.0303 (10)	0.0287 (10)	0.0283 (10)	0.0014 (8)	0.0115 (8)	0.0037 (8)
C3	0.0311 (10)	0.0302 (10)	0.0292 (10)	−0.0008 (8)	0.0116 (8)	0.0015 (8)
C4	0.0454 (13)	0.0515 (14)	0.0317 (11)	−0.0075 (10)	0.0141 (10)	−0.0073 (10)
C5	0.0325 (11)	0.0459 (12)	0.0393 (12)	−0.0015 (9)	0.0142 (9)	−0.0036 (10)
C6	0.0317 (10)	0.0326 (11)	0.0305 (10)	0.0015 (8)	0.0129 (8)	0.0018 (9)
C7	0.0303 (11)	0.0379 (11)	0.0340 (11)	0.0029 (8)	0.0178 (9)	0.0010 (9)
C8	0.0259 (10)	0.0378 (11)	0.0312 (10)	−0.0020 (8)	0.0151 (8)	−0.0034 (9)
C9	0.0281 (10)	0.0373 (11)	0.0330 (11)	−0.0026 (8)	0.0124 (9)	−0.0010 (9)
C10	0.0337 (11)	0.0530 (14)	0.0303 (11)	−0.0046 (9)	0.0107 (9)	−0.0028 (10)
C11	0.0475 (13)	0.0527 (15)	0.0372 (13)	−0.0062 (10)	0.0144 (10)	−0.0156 (11)
C12	0.0474 (13)	0.0382 (12)	0.0508 (14)	0.0008 (10)	0.0176 (11)	−0.0090 (11)
C13	0.0358 (11)	0.0356 (11)	0.0374 (12)	−0.0009 (9)	0.0149 (9)	−0.0018 (9)
C14	0.0541 (14)	0.0454 (14)	0.0386 (12)	0.0074 (10)	0.0105 (10)	0.0038 (10)
C15	0.0591 (15)	0.0417 (13)	0.0499 (14)	0.0078 (11)	0.0188 (12)	0.0070 (11)
N1	0.0316 (9)	0.0381 (9)	0.0289 (9)	−0.0014 (7)	0.0156 (7)	−0.0005 (7)
N2	0.0390 (10)	0.0462 (10)	0.0306 (9)	−0.0056 (8)	0.0150 (8)	−0.0052 (8)
N3	0.0378 (10)	0.0520 (12)	0.0409 (11)	−0.0065 (8)	0.0134 (8)	−0.0079 (9)
N4	0.0336 (9)	0.0488 (11)	0.0347 (9)	−0.0064 (8)	0.0175 (8)	−0.0098 (8)

C1—C7	1.347 (3)	C9—C10	1.395 (3)
C1—C2	1.456 (2)	C9—C14	1.510 (3)
C1—C8	1.493 (2)	C10—C11	1.372 (3)
C2—N1	1.332 (2)	C10—H10	0.9400
C2—N4	1.335 (2)	C11—C12	1.374 (3)
C3—N1	1.348 (2)	C11—H11	0.9400
C3—N2	1.358 (2)	C12—C13	1.382 (3)
C3—C6	1.413 (3)	C12—H12	0.9400
C4—N2	1.317 (3)	C13—C15	1.507 (3)
C4—N3	1.351 (3)	C14—H14A	0.9700
C4—H4	0.9400	C14—H14B	0.9700
C5—N3	1.323 (2)	C14—H14C	0.9700
C5—C6	1.391 (3)	C15—H15A	0.9700
C5—H5	0.9400	C15—H15B	0.9700
C6—C7	1.419 (3)	C15—H15C	0.9700
C7—H7	0.9400	N4—H4A	0.8700
C8—C9	1.392 (3)	N4—H4B	0.8700
C8—C13	1.408 (3)
C7—C1—C2	117.54 (17)	C9—C10—H10	119.3
C7—C1—C8	121.83 (16)	C10—C11—C12	119.9 (2)
C2—C1—C8	120.51 (16)	C10—C11—H11	120.1
N1—C2—N4	117.49 (16)	C12—C11—H11	120.1
N1—C2—C1	123.29 (17)	C11—C12—C13	121.0 (2)
N4—C2—C1	119.19 (17)	C11—C12—H12	119.5
N1—C3—N2	116.55 (16)	C13—C12—H12	119.5
N1—C3—C6	123.26 (17)	C12—C13—C8	118.86 (19)
N2—C3—C6	120.19 (17)	C12—C13—C15	120.24 (19)
N2—C4—N3	129.19 (19)	C8—C13—C15	120.89 (18)
N2—C4—H4	115.4	C9—C14—H14A	109.5
N3—C4—H4	115.4	C9—C14—H14B	109.5
N3—C5—C6	123.63 (18)	H14A—C14—H14B	109.5
N3—C5—H5	118.2	C9—C14—H14C	109.5
C6—C5—H5	118.2	H14A—C14—H14C	109.5
C5—C6—C3	116.98 (18)	H14B—C14—H14C	109.5
C5—C6—C7	125.45 (17)	C13—C15—H15A	109.5
C3—C6—C7	117.48 (17)	C13—C15—H15B	109.5
C1—C7—C6	120.61 (17)	H15A—C15—H15B	109.5
C1—C7—H7	119.7	C13—C15—H15C	109.5
C6—C7—H7	119.7	H15A—C15—H15C	109.5
C9—C8—C13	120.61 (17)	H15B—C15—H15C	109.5
C9—C8—C1	121.08 (17)	C2—N1—C3	117.76 (15)
C13—C8—C1	118.31 (17)	C4—N2—C3	115.93 (17)
C8—C9—C10	118.21 (19)	C5—N3—C4	114.02 (17)
C8—C9—C14	121.74 (17)	C2—N4—H4A	120.0
C10—C9—C14	120.05 (18)	C2—N4—H4B	120.0
C11—C10—C9	121.4 (2)	H4A—N4—H4B	120.0
C11—C10—H10	119.3

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N1i	0.87	2.18	3.044 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N1i	0.87	2.18	3.044 (2)	171

Symmetry code: (i) .