2,2-Bis(pyridin-2-yl)-1,3-diazinane.

In the title compound, C14H16N4, the six-membered hexa-hydro-pyrimidine ring adopts a chair conformation. In the crystal, one of the two pyrimidine N atoms engages in N-H⋯N hydrogen bonding with one of the pyridine N atoms, generating a helical chain running along the c axis. The helical pitch is the length of the c axis.

Related literature

For related structures, see: Song et al. (2010 ▶); Jayaratna & Norman (2010 ▶); Fun & Kia (2008 ▶); Warad et al. (2012 ▶). For competition between cyclization and bis­imine formation, see: Locke et al. (2009 ▶). For the use of hexa­hydro­pyrimidines as polydentate ligands for the synthesis of transition metal coordination complexes, see: Schmidt et al. (2011 ▶).

Experimental

Crystal data

C14H16N4

M = 240.31

Monoclinic,

a = 14.2372 (14) Å

b = 8.0302 (8) Å

c = 11.3277 (9) Å

β = 103.075 (8)°

V = 1261.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.3 × 0.2 × 0.15 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.98, T max = 0.99

4640 measured reflections

2238 independent reflections

1656 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 1.05

2238 reflections

171 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and ORTEP (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007459/nk2200sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007459/nk2200Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007459/nk2200Isup3.cml

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

C14H16N4	F(000) = 512
Mr = 240.31	Dx = 1.265 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1403 reflections
a = 14.2372 (14) Å	θ = 3.1–29.1°
b = 8.0302 (8) Å	µ = 0.08 mm−1
c = 11.3277 (9) Å	T = 293 K
β = 103.075 (8)°	Parallelpiped, colourless
V = 1261.5 (2) Å3	0.3 × 0.2 × 0.15 mm
Z = 4

Agilent Xcalibur Eos diffractometer	2238 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1656 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 16.0534 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −16→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→9
Tmin = 0.98, Tmax = 0.99	l = −13→13
4640 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0446P)2 + 0.061P] where P = (Fo2 + 2Fc2)/3
2238 reflections	(Δ/σ)max < 0.001
171 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.15 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
N3	0.79810 (10)	0.13990 (18)	0.07018 (11)	0.0369 (4)
N2	0.79269 (10)	0.05042 (18)	−0.24206 (10)	0.0406 (4)
N4	0.82606 (10)	0.32537 (17)	−0.08565 (12)	0.0377 (4)
C14	0.76709 (11)	0.18825 (19)	−0.05728 (12)	0.0315 (4)
C10	0.76853 (11)	0.03058 (19)	−0.13524 (12)	0.0306 (4)
C5	0.66284 (12)	0.2490 (2)	−0.08265 (13)	0.0356 (4)
C11	0.90172 (13)	0.1041 (2)	0.10491 (14)	0.0456 (5)
H11A	0.9148	0.0036	0.0640	0.055*
H11B	0.9198	0.0835	0.1915	0.055*
C9	0.74371 (12)	−0.1230 (2)	−0.09704 (14)	0.0412 (4)
H9A	0.7238	−0.1323	−0.0246	0.049*
N1	0.63469 (11)	0.3400 (2)	−0.18294 (12)	0.0511 (4)
C6	0.79561 (13)	−0.0872 (2)	−0.30852 (15)	0.0506 (5)
H6A	0.8117	−0.0751	−0.3832	0.061*
C13	0.92964 (13)	0.2875 (2)	−0.05846 (14)	0.0474 (5)
H13A	0.9651	0.3833	−0.0774	0.057*
H13B	0.9417	0.1947	−0.1078	0.057*
C12	0.96337 (13)	0.2441 (3)	0.07420 (15)	0.0532 (5)
H12A	0.9582	0.3410	0.1235	0.064*
H12B	1.0304	0.2098	0.0911	0.064*
C1	0.54414 (16)	0.3966 (3)	−0.20904 (18)	0.0639 (6)
H1A	0.5240	0.4598	−0.2790	0.077*
C7	0.77636 (14)	−0.2439 (2)	−0.27331 (15)	0.0520 (5)
H7A	0.7821	−0.3359	−0.3210	0.062*
C4	0.60138 (14)	0.2111 (3)	−0.00797 (16)	0.0539 (5)
H4A	0.6222	0.1458	0.0608	0.065*
C8	0.74829 (13)	−0.2622 (2)	−0.16589 (15)	0.0503 (5)
H8A	0.7327	−0.3666	−0.1403	0.060*
C2	0.47951 (15)	0.3674 (3)	−0.13943 (19)	0.0647 (6)
H2A	0.4174	0.4109	−0.1607	0.078*
C3	0.50821 (15)	0.2726 (3)	−0.03762 (19)	0.0685 (6)
H3A	0.4655	0.2496	0.0114	0.082*
H4	0.8042 (12)	0.352 (2)	−0.1662 (16)	0.052 (5)*
H3	0.7859 (12)	0.224 (2)	0.1143 (14)	0.050 (5)*

	U11	U22	U33	U12	U13	U23
N3	0.0487 (9)	0.0332 (8)	0.0296 (7)	0.0036 (7)	0.0108 (6)	−0.0032 (6)
N2	0.0533 (10)	0.0376 (9)	0.0329 (7)	−0.0027 (7)	0.0141 (6)	−0.0042 (6)
N4	0.0455 (9)	0.0288 (8)	0.0398 (8)	−0.0039 (7)	0.0120 (6)	−0.0006 (6)
C14	0.0390 (10)	0.0265 (9)	0.0301 (8)	0.0004 (7)	0.0102 (6)	−0.0010 (6)
C10	0.0353 (9)	0.0274 (9)	0.0286 (7)	0.0023 (7)	0.0059 (6)	−0.0010 (6)
C5	0.0408 (10)	0.0297 (9)	0.0368 (9)	−0.0001 (7)	0.0099 (7)	−0.0050 (7)
C11	0.0493 (12)	0.0495 (11)	0.0348 (9)	0.0080 (9)	0.0030 (7)	−0.0025 (8)
C9	0.0557 (12)	0.0320 (10)	0.0350 (9)	−0.0030 (8)	0.0087 (7)	0.0008 (7)
N1	0.0506 (10)	0.0521 (10)	0.0490 (9)	0.0117 (8)	0.0078 (7)	0.0072 (7)
C6	0.0613 (13)	0.0550 (13)	0.0374 (9)	0.0009 (10)	0.0154 (8)	−0.0131 (9)
C13	0.0426 (11)	0.0482 (12)	0.0529 (10)	−0.0101 (9)	0.0139 (8)	−0.0064 (8)
C12	0.0451 (12)	0.0599 (14)	0.0512 (10)	−0.0036 (10)	0.0039 (8)	−0.0127 (9)
C1	0.0583 (14)	0.0653 (15)	0.0618 (12)	0.0154 (11)	−0.0001 (10)	0.0046 (10)
C7	0.0639 (13)	0.0400 (12)	0.0462 (10)	0.0107 (10)	0.0004 (9)	−0.0178 (9)
C4	0.0487 (12)	0.0639 (14)	0.0528 (11)	0.0017 (10)	0.0190 (9)	0.0024 (9)
C8	0.0639 (13)	0.0279 (10)	0.0518 (11)	−0.0024 (9)	−0.0024 (9)	−0.0018 (8)
C2	0.0448 (13)	0.0705 (16)	0.0731 (14)	0.0124 (11)	0.0012 (10)	−0.0182 (12)
C3	0.0452 (13)	0.0887 (18)	0.0779 (15)	0.0000 (12)	0.0269 (10)	−0.0126 (13)

N3—C14	1.4635 (18)	N1—C1	1.336 (2)
N3—C11	1.467 (2)	C6—C7	1.367 (3)
N3—H3	0.878 (17)	C6—H6A	0.9300
N2—C10	1.3401 (18)	C13—C12	1.511 (2)
N2—C6	1.343 (2)	C13—H13A	0.9700
N4—C14	1.4638 (19)	C13—H13B	0.9700
N4—C13	1.468 (2)	C12—H12A	0.9700
N4—H4	0.921 (17)	C12—H12B	0.9700
C14—C5	1.527 (2)	C1—C2	1.361 (3)
C14—C10	1.546 (2)	C1—H1A	0.9300
C10—C9	1.379 (2)	C7—C8	1.372 (2)
C5—N1	1.334 (2)	C7—H7A	0.9300
C5—C4	1.381 (2)	C4—C3	1.384 (3)
C11—C12	1.514 (2)	C4—H4A	0.9300
C11—H11A	0.9700	C8—H8A	0.9300
C11—H11B	0.9700	C2—C3	1.365 (3)
C9—C8	1.373 (2)	C2—H2A	0.9300
C9—H9A	0.9300	C3—H3A	0.9300
C14—N3—C11	112.16 (12)	C7—C6—H6A	118.0
C14—N3—H3	107.7 (11)	N4—C13—C12	109.54 (14)
C11—N3—H3	108.3 (11)	N4—C13—H13A	109.8
C10—N2—C6	117.07 (15)	C12—C13—H13A	109.8
C14—N4—C13	113.39 (13)	N4—C13—H13B	109.8
C14—N4—H4	108.1 (11)	C12—C13—H13B	109.8
C13—N4—H4	110.8 (11)	H13A—C13—H13B	108.2
N3—C14—N4	110.86 (12)	C13—C12—C11	109.23 (14)
N3—C14—C5	109.51 (12)	C13—C12—H12A	109.8
N4—C14—C5	107.45 (13)	C11—C12—H12A	109.8
N3—C14—C10	107.83 (12)	C13—C12—H12B	109.8
N4—C14—C10	114.09 (12)	C11—C12—H12B	109.8
C5—C14—C10	106.97 (12)	H12A—C12—H12B	108.3
N2—C10—C9	121.72 (14)	N1—C1—C2	123.9 (2)
N2—C10—C14	117.23 (13)	N1—C1—H1A	118.0
C9—C10—C14	121.03 (13)	C2—C1—H1A	118.0
N1—C5—C4	122.15 (17)	C6—C7—C8	118.39 (16)
N1—C5—C14	115.30 (14)	C6—C7—H7A	120.8
C4—C5—C14	122.55 (15)	C8—C7—H7A	120.8
N3—C11—C12	113.15 (15)	C5—C4—C3	118.56 (19)
N3—C11—H11A	108.9	C5—C4—H4A	120.7
C12—C11—H11A	108.9	C3—C4—H4A	120.7
N3—C11—H11B	108.9	C7—C8—C9	118.52 (17)
C12—C11—H11B	108.9	C7—C8—H8A	120.7
H11A—C11—H11B	107.8	C9—C8—H8A	120.7
C8—C9—C10	120.09 (15)	C1—C2—C3	118.3 (2)
C8—C9—H9A	120.0	C1—C2—H2A	120.9
C10—C9—H9A	120.0	C3—C2—H2A	120.9
C5—N1—C1	117.65 (17)	C2—C3—C4	119.4 (2)
N2—C6—C7	124.09 (16)	C2—C3—H3A	120.3
N2—C6—H6A	118.0	C4—C3—H3A	120.3
C11—N3—C14—N4	−53.05 (17)	C10—C14—C5—C4	97.46 (17)
C11—N3—C14—C5	−171.44 (13)	C14—N3—C11—C12	53.15 (17)
C11—N3—C14—C10	72.50 (16)	N2—C10—C9—C8	3.5 (2)
C13—N4—C14—N3	56.96 (16)	C14—C10—C9—C8	−178.02 (15)
C13—N4—C14—C5	176.59 (11)	C4—C5—N1—C1	0.9 (3)
C13—N4—C14—C10	−65.00 (16)	C14—C5—N1—C1	−179.79 (15)
C6—N2—C10—C9	−2.7 (2)	C10—N2—C6—C7	−0.5 (3)
C6—N2—C10—C14	178.80 (14)	C14—N4—C13—C12	−58.22 (17)
N3—C14—C10—N2	−145.84 (13)	N4—C13—C12—C11	54.63 (19)
N4—C14—C10—N2	−22.22 (19)	N3—C11—C12—C13	−53.6 (2)
C5—C14—C10—N2	96.46 (16)	C5—N1—C1—C2	0.2 (3)
N3—C14—C10—C9	35.63 (19)	N2—C6—C7—C8	2.9 (3)
N4—C14—C10—C9	159.24 (14)	N1—C5—C4—C3	−1.2 (3)
C5—C14—C10—C9	−82.08 (17)	C14—C5—C4—C3	179.54 (16)
N3—C14—C5—N1	161.53 (13)	C6—C7—C8—C9	−2.0 (3)
N4—C14—C5—N1	41.03 (17)	C10—C9—C8—C7	−1.0 (2)
C10—C14—C5—N1	−81.87 (16)	N1—C1—C2—C3	−1.0 (3)
N3—C14—C5—C4	−19.1 (2)	C1—C2—C3—C4	0.6 (3)
N4—C14—C5—C4	−139.63 (16)	C5—C4—C3—C2	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2i	0.878 (17)	2.425 (18)	3.2845 (19)	166.4 (15)
N4—H4···N1	0.921 (17)	2.379 (17)	2.701 (2)	100.3 (12)
N4—H4···N2	0.921 (17)	2.564 (17)	2.8034 (19)	95.3 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2i	0.878 (17)	2.425 (18)	3.2845 (19)	166.4 (15)

Symmetry code: (i) .