4-Methyl-2,6-bis-(pyrrolidin-1-yl)pyrimidine.

In the crystal of the title compound, C13H20N4, the mol-ecule is nearly planar, the dihedral angles between the pyrimidine and the two pyrrolidine rings being 4.71 (2) and 4.50 (2)°. The crystal features inversion-related dimers linked by pairs of C-H⋯N hydrogen bonds generating R2(2)(16) patterns. The dimeric units are further linked into C(6) chains via an additional C-H⋯N hydrogen bond.

Related literature

For the synthesis and biological activity of pyrrolidine derivatives, see: Li et al. (2006 ▶); Lokhande et al. (2003 ▶); Imamura et al. (2004 ▶); Wyrzykiewicz, et al. (1993 ▶) and of pyrimidine derivatives, see: Holla et al. (2006 ▶); Zhao et al. (2007 ▶); Sondhi et al. (2005 ▶); Khalifa et al. (2005 ▶). For the graph-set description of hydrogen-bond motifs, see: Etter (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H20N4

M = 232.33

Triclinic,

a = 6.344 (3) Å

b = 8.766 (4) Å

c = 12.056 (6) Å

α = 79.10 (3)°

β = 86.05 (3)°

γ = 85.72 (3)°

V = 655.6 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.2 × 0.18 × 0.02 mm

Data collection

Bruker SMART X2S diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.986, T max = 0.999

8712 measured reflections

2302 independent reflections

1600 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.227

S = 1.13

2302 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2 and SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681204740X/bv2214sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204740X/bv2214Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204740X/bv2214Isup3.cml

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

C13H20N4	F(000) = 252
Mr = 232.33	Colourless
Triclinic, P1	Dx = 1.177 Mg m−3
Hall symbol: -P 1	Melting point: 446 K
a = 6.344 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.766 (4) Å	Cell parameters from 1600 reflections
c = 12.056 (6) Å	θ = 25°
α = 79.10 (3)°	µ = 0.07 mm−1
β = 86.05 (3)°	T = 296 K
γ = 85.72 (3)°	Prism, colorless
V = 655.6 (6) Å3	0.2 × 0.18 × 0.02 mm
Z = 2

Bruker SMART X2S diffractometer	2302 independent reflections
Radiation source: fine-focus steel tube	1600 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 1.03 pixels mm-1	θmax = 25°, θmin = 1.7°
phi and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.986, Tmax = 0.999	l = −14→14
8712 measured reflections

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.227	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.1307P)2 + 0.0781P] where P = (Fo2 + 2Fc2)/3
2302 reflections	(Δ/σ)max = 0.009
155 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.20 e Å−3
0 constraints

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	0.1352 (3)	0.2849 (2)	0.09361 (17)	0.0628 (6)
N2	0.0463 (3)	0.4541 (2)	0.21449 (16)	0.0540 (5)
N3	−0.0420 (3)	0.6226 (2)	0.33585 (17)	0.0645 (6)
N4	−0.1692 (3)	0.2415 (2)	0.21113 (17)	0.0642 (6)
C3	0.4251 (5)	0.2730 (3)	−0.0331 (3)	0.0869 (9)
H3A	0.4825	0.3359	−0.102	0.104*
H3B	0.5404	0.2102	0.0052	0.104*
C4	0.3118 (4)	0.3748 (3)	0.0424 (2)	0.0619 (7)
H4A	0.4029	0.3928	0.0994	0.074*
H4B	0.2625	0.4743	−0.001	0.074*
C5	0.0014 (3)	0.3283 (2)	0.17442 (19)	0.0535 (6)
C6	−0.0892 (3)	0.4968 (2)	0.29357 (18)	0.0534 (6)
C13	−0.1759 (4)	0.6913 (3)	0.4170 (2)	0.0730 (7)
H13A	−0.1876	0.6202	0.489	0.088*
H13B	−0.3164	0.72	0.3899	0.088*
C12	−0.0658 (6)	0.8320 (4)	0.4279 (3)	0.1077 (12)
H12A	−0.1492	0.9254	0.3963	0.129*
H12B	−0.0487	0.8332	0.507	0.129*
C2	0.2664 (5)	0.1735 (3)	−0.0592 (3)	0.0875 (9)
H2A	0.3319	0.0727	−0.0683	0.105*
H2B	0.2005	0.2212	−0.1287	0.105*
C1	0.1062 (5)	0.1559 (3)	0.0377 (2)	0.0761 (8)
H1A	−0.0358	0.162	0.0114	0.091*
H1B	0.1307	0.0571	0.0885	0.091*
C10	0.1473 (4)	0.7058 (3)	0.2981 (2)	0.0695 (7)
H10A	0.1459	0.7517	0.2183	0.083*
H10B	0.2742	0.6376	0.3112	0.083*
C9	−0.4898 (4)	0.2017 (3)	0.3329 (2)	0.0803 (8)
H9A	−0.4633	0.1377	0.4051	0.121*
H9B	−0.5157	0.1369	0.28	0.121*
H9C	−0.6114	0.2717	0.3406	0.121*
C7	−0.2678 (3)	0.4204 (3)	0.33417 (18)	0.0538 (6)
H7	−0.361	0.4543	0.3887	0.065*
C8	−0.3015 (3)	0.2932 (3)	0.29089 (19)	0.0567 (6)
C11	0.1343 (7)	0.8278 (5)	0.3691 (3)	0.1257 (14)
H11A	0.2446	0.8058	0.4228	0.151*
H11B	0.156	0.9284	0.3216	0.151*

	U11	U22	U33	U12	U13	U23
N1	0.0602 (12)	0.0608 (11)	0.0737 (13)	−0.0221 (9)	0.0104 (10)	−0.0268 (10)
N2	0.0506 (10)	0.0520 (10)	0.0626 (11)	−0.0116 (8)	−0.0004 (8)	−0.0165 (8)
N3	0.0629 (12)	0.0625 (11)	0.0740 (13)	−0.0178 (9)	0.0070 (10)	−0.0262 (10)
N4	0.0583 (12)	0.0643 (12)	0.0729 (13)	−0.0192 (9)	−0.0014 (10)	−0.0147 (10)
C3	0.091 (2)	0.0830 (18)	0.0925 (19)	−0.0260 (15)	0.0268 (16)	−0.0346 (15)
C4	0.0580 (14)	0.0593 (13)	0.0705 (15)	−0.0163 (11)	0.0054 (11)	−0.0156 (11)
C5	0.0503 (12)	0.0501 (12)	0.0620 (13)	−0.0119 (9)	−0.0048 (10)	−0.0114 (10)
C6	0.0514 (12)	0.0509 (12)	0.0585 (13)	−0.0055 (9)	−0.0055 (10)	−0.0101 (10)
C13	0.0802 (17)	0.0687 (15)	0.0744 (16)	−0.0084 (13)	0.0074 (13)	−0.0268 (13)
C12	0.101 (2)	0.089 (2)	0.148 (3)	−0.0174 (17)	0.020 (2)	−0.064 (2)
C2	0.094 (2)	0.0767 (18)	0.101 (2)	−0.0113 (15)	0.0081 (17)	−0.0419 (16)
C1	0.0868 (18)	0.0655 (15)	0.0851 (17)	−0.0225 (13)	0.0056 (15)	−0.0336 (13)
C10	0.0694 (15)	0.0633 (14)	0.0805 (17)	−0.0199 (12)	−0.0011 (13)	−0.0202 (13)
C9	0.0626 (15)	0.0877 (18)	0.0879 (18)	−0.0281 (13)	0.0078 (13)	−0.0044 (15)
C7	0.0492 (12)	0.0566 (12)	0.0560 (13)	−0.0066 (10)	0.0063 (10)	−0.0135 (10)
C8	0.0467 (12)	0.0611 (13)	0.0599 (13)	−0.0095 (10)	−0.0023 (10)	−0.0026 (11)
C11	0.152 (3)	0.120 (3)	0.129 (3)	−0.076 (2)	0.049 (3)	−0.077 (2)

N1—C5	1.339 (3)	C12—C11	1.412 (5)
N1—C1	1.451 (3)	C12—H12A	0.97
N1—C4	1.452 (3)	C12—H12B	0.97
N2—C6	1.328 (3)	C2—C1	1.488 (4)
N2—C5	1.341 (3)	C2—H2A	0.97
N3—C6	1.360 (3)	C2—H2B	0.97
N3—C13	1.440 (3)	C1—H1A	0.97
N3—C10	1.453 (3)	C1—H1B	0.97
N4—C8	1.353 (3)	C10—C11	1.486 (4)
N4—C5	1.369 (3)	C10—H10A	0.97
C3—C2	1.467 (4)	C10—H10B	0.97
C3—C4	1.505 (3)	C9—C8	1.494 (3)
C3—H3A	0.97	C9—H9A	0.96
C3—H3B	0.97	C9—H9B	0.96
C4—H4A	0.97	C9—H9C	0.96
C4—H4B	0.97	C7—C8	1.354 (3)
C6—C7	1.373 (3)	C7—H7	0.93
C13—C12	1.492 (4)	C11—H11A	0.97
C13—H13A	0.97	C11—H11B	0.97
C13—H13B	0.97
C5—N1—C1	124.27 (19)	H12A—C12—H12B	108.3
C5—N1—C4	123.00 (19)	C3—C2—C1	106.7 (2)
C1—N1—C4	112.31 (19)	C3—C2—H2A	110.4
C6—N2—C5	116.30 (18)	C1—C2—H2A	110.4
C6—N3—C13	124.4 (2)	C3—C2—H2B	110.4
C6—N3—C10	122.3 (2)	C1—C2—H2B	110.4
C13—N3—C10	113.3 (2)	H2A—C2—H2B	108.6
C8—N4—C5	115.7 (2)	N1—C1—C2	104.37 (19)
C2—C3—C4	106.1 (2)	N1—C1—H1A	110.9
C2—C3—H3A	110.5	C2—C1—H1A	110.9
C4—C3—H3A	110.5	N1—C1—H1B	110.9
C2—C3—H3B	110.5	C2—C1—H1B	110.9
C4—C3—H3B	110.5	H1A—C1—H1B	108.9
H3A—C3—H3B	108.7	N3—C10—C11	102.9 (2)
N1—C4—C3	103.21 (19)	N3—C10—H10A	111.2
N1—C4—H4A	111.1	C11—C10—H10A	111.2
C3—C4—H4A	111.1	N3—C10—H10B	111.2
N1—C4—H4B	111.1	C11—C10—H10B	111.2
C3—C4—H4B	111.1	H10A—C10—H10B	109.1
H4A—C4—H4B	109.1	C8—C9—H9A	109.5
N1—C5—N2	116.98 (19)	C8—C9—H9B	109.5
N1—C5—N4	118.4 (2)	H9A—C9—H9B	109.5
N2—C5—N4	124.6 (2)	C8—C9—H9C	109.5
N2—C6—N3	116.4 (2)	H9A—C9—H9C	109.5
N2—C6—C7	123.7 (2)	H9B—C9—H9C	109.5
N3—C6—C7	119.8 (2)	C8—C7—C6	116.7 (2)
N3—C13—C12	103.8 (2)	C8—C7—H7	121.7
N3—C13—H13A	111	C6—C7—H7	121.7
C12—C13—H13A	111	N4—C8—C7	123.0 (2)
N3—C13—H13B	111	N4—C8—C9	117.2 (2)
C12—C13—H13B	111	C7—C8—C9	119.8 (2)
H13A—C13—H13B	109	C12—C11—C10	110.0 (3)
C11—C12—C13	108.7 (3)	C12—C11—H11A	109.7
C11—C12—H12A	110	C10—C11—H11A	109.7
C13—C12—H12A	110	C12—C11—H11B	109.7
C11—C12—H12B	110	C10—C11—H11B	109.7
C13—C12—H12B	110	H11A—C11—H11B	108.2

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···N3i	0.97 (1)	2.82	3.793 (2)	175
C9—H9C···N2ii	0.96 (1)	2.93	3.742 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯N3i	0.97 (1)	2.82	3.793 (2)	175
C9—H9C⋯N2ii	0.96 (1)	2.93	3.742 (2)	143

Symmetry codes: (i) ; (ii) .